ars.els-cdn.com · Web viewTLC information was recorded on GF 254 (Qingdao Haiyang Chemical Co.,...
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Supporting information Conten t 1 General information...........................................2 2.1 General procedure A for synthesis of α-haloamide............2 2.2 General procedure A for synthesis of nitrones...............2 2.3 General Procedure B for the [3+3]-cycloaddition of nitrones with α-halo amides:.............................................3 3 Structure characterization....................................3 4 NMR spectra...................................................9 5 X-Ray diffraction of (3R,6S)-4-(benzyloxy)-2-methyl-6-phenyl-3- (p-tolyl)-1,2,4- oxadiazinan-5–one.............................38 1 / 43
Transcript of ars.els-cdn.com · Web viewTLC information was recorded on GF 254 (Qingdao Haiyang Chemical Co.,...
Supporting information
Conten
t
1 General information.......................................................................................................................2
2.1 General procedure A for synthesis of α-haloamide.....................................................................2
2.2 General procedure A for synthesis of nitrones............................................................................2
2.3 General Procedure B for the [3+3]-cycloaddition of nitrones with α-halo amides:....................3
3 Structure characterization..............................................................................................................3
4 NMR spectra..................................................................................................................................9
5 X-Ray diffraction of (3R,6S)-4-(benzyloxy)-2-methyl-6-phenyl-3-(p-tolyl)-1,2,4- oxadiazinan-
5–one..............................................................................................................................................38
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1 General Information All reactions were carried out under an atmosphere of nitrogen in oven-dried
glassware with magnetic stirring, unless otherwise specified. Dichloromethane was purified by passage through a bed of activated alumina. All other reagents and solvents were purchased from Sigma-Aldrich or J&K Chemical Company and used without any further purification. TLC information was recorded on GF 254 (Qingdao Haiyang Chemical Co., Ltd. P. R. China) plates and developed by staining with KMnO4 or ceric ammonium molybdate (CAM). Purification of reaction products was carried out by flash chromatography using Silica gel (200 - 300 mesh, Qingdao Haiyang Chemical Co. Ltd. P. R. China). 1H NMR spectra were measured on Varian 400 (400 MHz), spectrometers and are reported in ppm (s=singlet, d=doublet, t=triplet, q=quartet, m=multiplet, br=broad; integration; coupling constant(s) in Hz), using TMS as an internal standard (TMS at 0.00 ppm) in CDCl3. 13C NMR spectra were recorded on V400 spectrometer and reported in ppm using solvent as an internal standard (CDCl3 at 77.16 ppm). High-resolution mass spectra were obtained using an Agilent 6230 TOF LC/MS with an (atmospheric pressure photo-ionization (APPI) or electrospray (ESI) source with purine and HP-0921 as an internal calibrants. HRMS (EI) was performed on an API-Qstar-Pulsar-1 spectrometer.
2.1 General procedure A for the synthesis of α-haloamide
To a solution of O-benzylhydroxylamine HCl (1 g, 6.3 mmol) in dicholoromethane (30 mL), trimethylamine (0.88 mL, 6.3 mmol) was added. The reaction mixture was then cooled to 0 ºC. Next, 2-bromo-2-methylpropanoyl bromide (0.75 mL, 6.3 mmol) was added dropwise to the reaction mixture. The reaction was stirred for 4 h at 0 ºC. After 4 h, the reaction mixture was then allowed to warm to room temperature and was quenched with water. The resulting mixture was then washed with brine (3 times). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The crude reaction mixture was purified by silica gel chromatography (ethyl acetate/hexanes) to give haloamide as a white solid (1.3 g, 80%).
2.2 General procedure A for the synthesis of nitrones
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To a solution of hydroxylamine hydrochloride (1.0 mmol) in the water (2.0 mL) was added aldehyde (1.0 mmol) and NaOH (1.0 mmol), the reaction mixture was stirred at room temperature until completion, the aqueous phase extracted with CH2Cl2 (3 x 10 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to give nitrones.
2.3 General procedure B for the [3+3]-cycloaddition of nitrones with α-halo amides:
To a solution of nitrones 2 (1.1 mmol) in CH3CN (2.0 mL) was added α-haloamide 1 (1.0 mmol.) and sodium carbonate (2.0 mmol) and stirred at 50oC and the reaction progress monitored by TLC (hexane : ethyl acetate = 5:1) until complete consumption of the α-haloamide (reaction time: see substrate tables). The mixture was filtered through the short pad of celite and the filtrate was concentrated under reduced pressure. The residue was purified via flash column chromatography (hexane : ethyl acetate = 15:1 to 10:1) to provide the desired cycloadducts.
3. Structure characterization(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-phenyl-1,2,4-oxadiazinan-5-one (3a)
Colorless oil, 98% yield. 1H NMR (400 MHz, CDCl3): δ 7.46-7.43 (m, 5H), 7.31-7.28 (m, 3H), 7.07-7.05 (m, 2H), 5.02 (d, 1H, J= 9.7Hz), 4.87 (s, 1H), 4.81 (q, 1H, J= 6.9Hz), 4.31 (d, 1H, J= 9.7Hz), 2.41 (s, 3H), 1.50 (d, 3H, J= 6.9Hz); 13C NMR (100 MHz, CDCl3): δ 168.1, 134.7, 134.1, 130.0, 129.8, 129.1, 128.8, 128.7, 128.4, 88.2, 77.3, 77.1, 41.6, 15.2. HRMS (EI) m/z
335.1372 [M+Na]+ (calcd for C18H20N2O3Na 335.1372).
(3R,6S)-4-(benzyloxy)-3-(2-chlorophenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3b)Colorless oil, 85% yield. 1H NMR (400 MHz, CDCl3): δ 7.44-7.19 (m, 9H), 5.06 (d, 1H, J= 10.1Hz), 4.90 (s, 1H), 4.64-4.58 (m, 2H), 2.37 (s, 3H), 1.65 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.6, 135.6, 134.6, 134.5, 130.0, 129.8, 129.7, 129.2, 129.0, 128.5, 127.3, 85.2, 77.5, 77.2, 41.1, 16.5.
HRMS (EI) m/z 369.0982 [M+Na]+ (calcd for C18H19ClN2O3Na 369.0982).
(3R,6S)-4-(benzyloxy)-3-(2-methoxyphenyl)-2,6-dimethyl-1,2,4-oxadiazinan-
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5-one (3c)Colorless oil, 78% yield. 1H NMR (400 MHz, CDCl3): δ 7.42-7.36 (m, 2H), 7.31-7.28 (m, 3H), 7.24-7.22 (m, 2H), 7.05-7.01 (m, 1H), 6.95 (d, 1H, J= 8.0Hz), 5.82 (s, 1H), 5.07 (d, 1H, J= 10.1Hz), 4.74 (d, 1H, J= 10.1Hz), 4.66 (q, 1H, J= 7.1Hz), 3.82 (s, 3H), 2.41 (s, 3H), 1.61 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.8, 158.3, 135.0, 130.5, 130.0, 129.4, 128.6, 128.3, 121.2, 120.7, 110.6, 77.2, 77.0, 55.6, 40.3, 16.2. HRMS (EI) m/z 365.1477 [M+Na]+ (calcd for C19H22N2O4Na 365.1477).
(3R,6S)-4-(benzyloxy)-3-(3-chlorophenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3d)Colorless oil, 89% yield. 1H NMR (400 MHz, CDCl3): δ 7.44-7.19 (m, 9H), 5.06 (d, 1H, J= 10.1Hz), 4.90 (s, 1H), 4.64-4.58 (m, 2H), 2.37 (s, 3H), 1.65 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.6, 135.4, 134.7, 134.5, 130.0, 129.8, 129.7, 129.2, 129.0, 128.5, 127.3, 85.2, 77.5, 77.2, 41.1, 16.5. HRMS (EI) m/z 369.0982 [M+Na]+ (calcd for C18H19ClN2O3Na 369.0982).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(3-nitrophenyl)-1,2,4-oxadiazinan-5-one (3e)Colorless oil, 81% yield. 1H NMR (400 MHz, CDCl3): δ 8.29-8.26 (m, 1H), 8.09-8.08 (m, 1H), 7.65-7.57 (m, 2H), 7.34-7.28 (m, 3H), 7.22-7.19 (m, 2H), 5.05 (d, 1H, J= 10.0Hz), 4.99 (s, 1H), 4.76 (d, 1H, J= 10.0Hz), 4.69 (q, 1H, J= 7.1Hz), 2.35 (s, 3H), 1.64 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.7, 148.1, 135.7, 134.8, 134.7, 129.6, 129.5, 129.1, 128.6, 124.5, 124.1, 84.6,
77.4, 77.3, 41.0, 16.3. HRMS (EI) m/z 380.1222 [M+Na]+ (calcd for C18H19N3O5Na 380.1222).
(3R,6S)-4-(benzyloxy)-3-(4-chlorophenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3f)Colorless oil, 91% yield. 1H NMR (400 MHz, CDCl3): δ 7.41-7.39 (m, 2H), 7.34-7.27 (m, 5H), 7.20-7.18 (m, 2H), 5.05 (d, 1H, J= 10.0Hz), 4.92 (s, 1H), 4.64-4.58 (m, 2H), 2.35 (s, 3H), 1.63 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.7, 135.7, 134.7, 132.1, 130.4, 129.6, 128.9,
128.8, 128.5, 85.1, 77.4, 77.2, 41.0, 16.5. HRMS (EI) m/z 369.0985 [M+Na]+ (calcd for C18H19ClN2O3Na 369.0982).
(3R,6S)-4-(benzyloxy)-3-(4-fluorophenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3g)Colorless oil, 93% yield. 1H NMR (400 MHz, CDCl3): δ 7.36-7.28 (m, 5H), 7.19-7.10 (m, 4H), 5.05 (d, 1H, J= 10.1Hz), 4.94 (s, 1H), 4.63 (q, 1H, J= 7.0Hz), 4.55 (d, 1H, J= 10.1Hz), 2.35 (s, 3H), 1.64 (d, 3H, J= 7.0Hz); 13C NMR (100 MHz, CDCl3): δ 167.7, 164.7, 162.2, 134.7, 130.9, 130.8, 129.6,
129.5, 128.9, 128.5, 115.7, 115.5, 85.2, 77.4, 77.2, 41.0, 16.5. HRMS (EI) m/z 353.1275 [M+Na]+
(calcd for C18H19FN2O3Na 353.1277).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(p-tolyl)-1,2,4-oxadiazinan-5-
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one(3h)Colorless oil, 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.39-7.16 (m, 9H), 5.05 (d, 1H, J= 10.1Hz)，4.93 (s, 1H), 4.60 (q, 1H, J= 7.1Hz), 4.52 (d, 1H, J= 10.1Hz), 2.42 (s, 3H), 2.38 (s, 3H), 1.66 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.9, 139.7, 134.8, 130.5, 129.6, 129.2, 129.1, 128.7, 128.4, 85.8, 77.2, 41.0, 21.3, 16.6. HRMS (EI) m/z 349.1509 [M+Na]+ (calcd for C19H22N2O3Na 349.1528).
(3R,6S)-4-(benzyloxy)-3-(4-methoxyphenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3i)Colorless oil, 96% yield. 1H NMR (400 MHz, CDCl3): δ 7.43-7.29 (m, 5H), 7.19-7.17 (m, 2H), 6.96-6.94 (m, 2H), 5.04 (d, 1H, J= 10.1Hz), 4.93 (s, 1H), 4.60 (q, 1H, J= 7.1Hz), 4.51 (d, 1H, J= 10.1Hz), 3.86 (s, 3H), 2.36 (s, 3H), 1.66 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz,
CDCl3): δ 167.7, 160.7, 134.8, 130.4, 129.6, 129.5, 128.8, 128.4, 113.9, 85.6, 77.2, 55.4, 41.0, 16.6. HRMS (EI) m/z 365.1477 [M+Na]+ (calcd for C19H22N2O4Na 365.1477).
(3R,6S)-4-(benzyloxy)-3-(4-(dimethylamino)phenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3j)Colorless oil, 87% yield. 1H NMR (400 MHz, CDCl3): δ 7.31-7.28 (m, 4H), 7.23-7.18 (m, 3H), 6.74 (d, 2H, J= 9.2Hz), 5.05 (d, 1H, J= 10.1Hz), 4.89 (s, 1H), 4.60 (q, 1H, J= 7.1Hz), 4.50 (d, 1H, J= 10.1Hz), 3.02 (s, 6H), 2.37 (s, 3H), 1.65 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ
167.7, 151.3, 135.0, 130.1, 129.7, 128.7, 128.3, 120.5, 111.8, 100.0, 77.1, 41.1, 40.4, 16.7. HRMS (EI) m/z 378.1795 [M+Na]+ (calcd for C20H25N3O3Na 378.1794).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(4-nitrophenyl)-1,2,4-oxadiazinan-5-one (3k)Colorless oil, 85% yield. 1H NMR (400 MHz, CDCl3): δ 8.24 (d, 2H, J= 12Hz), 7.47-7.19 (m, 7H), 5.04 (d, 1H, J= 10.1Hz), 5.00 (s, 1H), 4.71 (d, 1H, J= 10.1Hz), 4.67 (q, 1H, J= 7.1Hz), 2.36 (s, 3H), 1.61 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.7, 148.7, 140.6, 134.6,
130.0, 129.6, 129.1, 128.6, 123.6, 84.5, 77.2, 40.9, 16.2. HRMS (EI) m/z 380.1220 [M+Na]+
(calcd for C18H19N3O5Na 380.1222).
(3R,6S)-4-(benzyloxy)-3-(2,4-dichlorophenyl)-2,6-dimethyl-1,2,4-oxadiazinan-5-one (3l)Colorless oil, 83% yield. 1H NMR (400 MHz, CDCl3): δ 7.44-7.28 (m, 8H), 5.72 (s, 1H), 5.06 (d, 1H, J= 10.1Hz), 4.82 (d, 1H, J= 10.1Hz), 4.68 (q, 1H, J= 7.0Hz), 2.43 (s, 3H), 1.60 (d, 3H, J= 7.0Hz); 13C NMR (100 MHz, CDCl3): δ 167.6, 135.9, 135.5, 134.6, 131.3, 129.6, 129.4, 128.9,
127.5, 79.6, 77.4, 77.2, 40.2, 16.1. HRMS (EI) m/z 403.0596[M+Na]+ (calcd for C18H18Cl2N2O3Na 403.0592).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(naphthalen-2-yl)-1,2,4-
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oxadiazinan-5-one (3m) Colorless oil, 89% yield. 1H NMR (400 MHz, CDCl3): δ 7.91-7.77 (m, 4H), 7.59-7.57 (m, 3H), 7.29-7.21 (m, 3H), 7.10 (d, 2H, J= 6.3Hz), 5.15 (s, 1H), 5.09 (d, 1H, J= 10.0Hz), 4.69 (q, 1H, J= 6.5Hz), 4.53 (d, 1H, J= 10.0Hz), 2.41 (s, 3H), 1.75 (d, 3H, J= 6.5Hz); 13C NMR (100 MHz, CDCl3): δ 167.8, 134.7, 134.0, 132.8, 131.1, 129.7, 129.5, 128.8, 128.5, 128.4, 128.2, 127.9, 127.0, 126.6, 125.6,86.3, 77.5, 77.3, 41.2, 16.7. HRMS (EI) m/z 385.1533 [M+Na]+ (calcd for C22H22N2O3Na 385.1528).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(thiophen-2-yl)-1,2,4-oxadiazinan-5-one (3n)Colorless oil, 98% yield. 1H NMR (400 MHz, CDCl3): δ 7.45 (d,1H, J= 5.0Hz), 7.34-7.27 (m, 5H), 7.15-7.06 (m, 2H), 5.36 (s, 1H), 5.08 (d, 1H, J= 10.1Hz), 4.67 (q, 1H, J= 7.1Hz), 4.55 (d, 1H, J= 10.1Hz), 2.45 (s, 3H), 1.59 (d, 3H, J=
7.1Hz); 13C NMR (100 MHz, CDCl3): δ 166.9, 135.7, 134.7, 129.8, 129.6, 128.8, 128.4, 128.3, 126.2, 81.0, 77.8, 77.5, 40.7, 31.0, 15.9. HRMS (EI) m/z 341.0936 [M+Na]+ (calcd for C16H18N2O3SNa 341.0936).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(pyridin-3-yl)-1,2,4-oxadiazinan-5-one (3o)Colorless oil, 78% yield. 1H NMR (400 MHz, CDCl3): δ 8.70-8.50 (m, 1H), 8.50 (s, 1H) 7.71-7.68 (m, 1H), 7.38-7.20 (m, 6H), 5.06 (d, 1H, J= 10.1Hz), 4.95 (s, 1H), 4.68-4.66 (m, 2H), 2.36 (s, 3H), 1.63 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.7, 151.1, 150.4, 136.4, 134.6, 129.6, 129.0, 128.6,
123.6, 83.5, 77.4, 41.0, 16.3. HRMS (EI) m/z 336.1324 [M+Na]+ (calcd for C17H19N3O3Na 336.1324).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-((E)-styryl)-1,2,4-oxadiazinan-5-one (3p)Colorless oil, 82% yield. 1H NMR (400 MHz, CDCl3): δ 7.46-7.32 (m, 10H), 6.66-6.60 (m, 1H), 6.34-6.28 (m, 1H), 5.11 (d, 1H, J= 10.1Hz), 4.95 (d, 1H, J= 10.1Hz), 4.62-4.59 (m, 2H), 2.59 (s, 3H), 1.52 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.3, 138.0, 135.4, 135.3, 129.8,
128.9, 128.8, 128.5, 127.0, 121.7, 84.7, 77.2, 40.9, 16.0. HRMS (EI) m/z 361.1528 [M+Na]+
(calcd for C20H22N2O3Na 361.1528).
(3R,6S)-4-(benzyloxy)-2,6-dimethyl-3-(phenylethynyl)-1,2,4-oxadiazinan-5-one (3q)Colorless oil, 81% yield. 1H NMR (400 MHz, CDCl3): δ 7.53-7.50 (m, 5H), 7.42-7.36 (m, 5H), 5.29 (d, 1H, J= 10.1Hz), 5.20 (d, 1H, J= 10.1Hz), 5.10 (s, 1H), 4.59 (q, 1H, J= 7.1Hz), 2.83 (s, 3H), 1.53 (d, 3H, J= 7.1Hz); 13C NMR
(100 MHz, CDCl3): δ 167.1, 134.8, 132,0, 129.7, 129.4, 128.9, 128.8, 128.5, 127.4, 121.3, 100.4, 88.1, 80.8, 77.4, 41.8, 15.9. HRMS (EI) m/z 359.1374 [M+Na]+ (calcd for C20H20N2O3Na 359.1372).
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(3R,6S)-2-benzyl-4-(benzyloxy)-6-methyl-3-phenyl-1,2,4-oxadiazinan-5-one (3r)Colorless oil, 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.51-7.17 (m, 15H), 5.18 (s, 1H), 5.13 (d, 1H, J= 10.1Hz), 4.61 (q, 1H, J= 7.1Hz), 4.51 (d, 1H, J= 10.1Hz), 3.69 (d, 1H, J= 12.8Hz), 3.55 (d, 1H, J= 12.8Hz), 1.54 (d, 3H, J=
7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.8, 135.9, 134.7, 133.8, 130.1, 129.9, 129.8, 129.7, 129.4, 128.9, 128.8, 128.7, 128.5, 128.4, 128.3, 128.2, 127.6, 127.4, 84.1, 77.5, 77.4, 57.1, 16.5. HRMS (EI) m/z 411.1683 [M+Na]+ (calcd for C24H24N2O3Na 411.1685).
(3R,6S)-2-benzyl-4-(benzyloxy)-6-methyl-3-(p-tolyl)-1,2,4-oxadiazinan-5-one (3s)Colorless oil, 92% yield. 1H NMR (400 MHz, CDCl3): δ 7.35-7.18 (m, 14H), 5.13 (s, 1H), 5.09 (d, 1H, J= 10.1Hz), 4.58 (q, 1H, J= 7.1Hz), 4.53 (d, 1H, J= 10.1Hz), 3.68 (d, 1H, J= 10.1Hz), 3.52 (d, 1H, J= 10.1Hz), 2.45 (s, 3H), 1.52 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.8, 139.8, 136.0,
134.8, 130.8, 129.7, 129.3, 129.2, 128.8, 128.4, 128.3, 127.5, 84.0, 77.4, 57.1, 21.4, 16.4. HRMS (EI) m/z 425.1841 [M+Na]+ (calcd for C25H26N2O3Na 425.1841).
(3R,6S)-2-benzyl-4-(benzyloxy)-3-(4-chlorophenyl)-6-methyl-1,2,4-oxadiazinan-5-one (3t)Colorless oil, 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.44-7.19 (m, 14H), 5.09 -5.03(m, 2H), 4.61-4.58 (m, 2H), 3.65 (d, 1H, J= 10.1Hz), 3.50 (d, 1H, J= 10.1Hz), 1.50 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ
167.8, 135.7, 135.4, 134.7, 132.3, 130.6, 129.8, 129.6, 129.0, 128.9, 128.8, 128.7, 128.5, 128.4, 128.3, 127.7, 83.2, 77.5, 57.1, 16.2. HRMS (EI) m/z 445.1298 [M+Na]+ (calcd for C24H23N2ClO3Na 445.1295).
(3R,6S)-2-benzyl-4-(benzyloxy)-6-methyl-3-(thiophen-2-yl)-1,2,4-oxadiazinan-5-one (3u)Colorless oil, 96% yield. 1H NMR (400 MHz, CDCl3): δ 7.51-7.49 (m,1H), 7.34-7.24 (m, 10H), 7.10-7.09 (m, 2H), 5.43 (s, 1H), 5.08 (d, 1H, J= 10.1Hz)， 4.87 (q, 1H J= 7.1Hz), 4.50 (d, 1H, J= 10.1Hz), 3.88 (d, 1H, J=
13.3Hz), 3.57 (d, 1H, J= 13.3Hz), 1.54 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.0, 135.9, 135.2, 134.7, 130.0, 129.6, 128.9, 128.8, 128.5, 128.4, 127.8, 126.2, 79.3, 78.0, 77.8, 57.1, 15.9. HRMS (EI) m/z 417.1249 [M+Na]+ (calcd for C22H22N2O3SNa 417.1249).
(3R,6S)-4-(benzyloxy)-6-ethyl-2-methyl-3-phenyl-1,2,4-oxadiazinan-5-one (4a)Colorless oil, 96% yield. 1H NMR (400 MHz, CDCl3): δ 7.47-7.41 (m, 5H), 7.32-7.27 (m, 3H), 7.12 (m, 2H), 5.06 (d, 1H, J= 10.1Hz), 4.95 (s, 1H), 4.43 (d, 1H, J= 10.1Hz), 4.36 (dd, 1H, J1= 5.7Hz, J2= 3.8Hz)，2.39 (s, 1H), 2.23-
2.06 (m, 2H), 1.12 (t, 3H, J= 7.5Hz); 13C NMR (100 MHz, CDCl3): δ 167.5, 134.7, 133.9, 129.8, 129.6, 129.2, 128.9, 128.6, 128.4, 85.4, 82.2, 41.2, 24.1, 10.3. HRMS (EI) m/z 349.1530 [M+Na]+
(calcd for C19H22N2O3Na 349.1528).
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(3R,6S)-4-(benzyloxy)-2-methyl-3,6-diphenyl-1,2,4-oxadiazinan-5-one (4b)Colorless oil, 94% yield. 1H NMR (400 MHz, CDCl3): δ 7.67 (d, 2H, J= 4Hz), 7.51-7.43 (m, 9H), 7.34 (m, 3H), 7.16-7.14 (m, 2H), 5.58 (s, 1H), 5.18-5.16 (m, 2H), 4.43 (d, 1H, J= 10.1Hz), 2.44 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 165.7, 136.2, 134.6, 133.8, 130.0, 129.9, 129.7, 129.3,
129.0, 128.9, 128.7, 128.6, 128.5, 128.4, 127.7, 86.9, 82.4, 77.7, 41.4. HRMS (EI) m/z 397.1526 [M+Na]+ (calcd for C23H22N2O3Na 397.1528).
(3R,6S)-4-(benzyloxy)-6-chloro-2-methyl-3-phenyl-1,2,4-oxadiazinan-5-one (4c)Colorless oil, 76% yield. 1H NMR (400 MHz, CDCl3): δ 7.54-7.48 (m, 5H), 7.33-7.29 (m, 3H), 7.00-6.98 (m, 2H), 6.14 (s, 1H), 5.08 (d, 1H, J= 10.1Hz), 5.01 (s, 1H), 4.24 (d, 1H, J= 10.1Hz), 2.53 (s, 3H); 13C NMR (100 MHz,
CDCl3): δ 160.7, 134.0, 132.7, 130.7 129.8, 129.0, 128.4, 128.3, 87.4, 85.9, 77.7, 41.7. HRMS (EI) m/z 355.0825 [M+Na]+ (calcd for C17H17N2O3ClNa 355.0825).
(R)-4-(benzyloxy)-6,6-dichloro-2-methyl-3-phenyl-1,2,4-oxadiazinan-5-one (4d)Colorless oil, 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.51-7.45 (m, 3H), 7.39-7.33 (m, 5H), 7.18-7.16 (m, 2H), 5.08 (d, 1H, J= 10.1Hz), 4.95 (s, 1H), 4.54 (d, 1H, J= 10.1Hz), 2.53 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 158.5,
134.0, 131.4, 130.7, 130.1, 129.3, 129.0, 128.7, 128.6, 128.5, 128.4, 106.5, 85.6, 41,4. HRMS (EI) m/z 389.0432 [M+Na]+ (calcd for C17H16N2O3Cl2Na 389.0436).
(R)-4-(benzyloxy)-2,6,6-trimethyl-3-phenyl-1,2,4-oxadiazinan-5-one (4e)Colorless oil, 96% yield. 1H NMR (400 MHz, CDCl3): δ 7.47-7.38 (m, 5H), 7.32-7.28 (m, 3H), 7.13-7.11 (m, 2H), 5.00 (d, 1H, J= 10.1Hz), 4.89 (s, 1H), 4.40 (d, 1H, J= 10.1Hz), 2.35 (s, 3H), 1.71 (s, 3H), 1.51 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 170.6, 134.7, 133.9, 129.9, 129.8, 129.1, 128.8, 128.6, 128.4,
81.8, 77.1, 41.3, 24.1, 23.9. HRMS (EI) m/z 349.1525[M+Na]+ (calcd for C19H22N2O3Na 349.1528).
(3R,6S)-4-methoxy-2,6-dimethyl-3-phenyl-1,2,4-oxadiazinan-5-one (4f)Colorless oil, 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.43 (s, 5H), 5.19 (s, 1H), 4.60 (q, 1H, J= 7.1Hz), 3.57 (s, 3H), 2.41 (s, 3H), 1.62 (d, 3H, J= 7.1Hz); 13C NMR (100 MHz, CDCl3): δ 167.4, 133.5, 129.8, 129.1, 128.5, 84.8, 77.2, 62.9, 41.0, 16.4. HRMS (EI) m/z 259.1057 [M+Na]+ (calcd for C12H16N2O3Na 259.1059).
4-(benzyloxy)-3-(2-chlorophenyl)-2-methyl-6-phenyl-1,2,4-oxadiazinan-5-one (4g)Colorless oil, 80% yield. 1H NMR (400 MHz, CDCl3): δ 7.62-7.59 (m, 3H),
8 / 39
7.48-7.23 (m, 11H), 5.99 (s, 1H), 5.59 (s, 1H), 5.15 (d, 1H, J= 10.1Hz), 4.68 (d, 1H, J= 10.1Hz), 2.51 (s, 3H), 2.19 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 165.7, 135.1, 134.4, 131.1, 130.8, 129.8, 129.5, 128.8, 128.6.128.5, 128.4, 127.7, 127.3, 82.4, 77.4, 40.6, 31.0. HRMS (EI) m/z 411.1685 [M+Na]+ (calcd for C24H24N2O3Na 411.1685).4 NMR spectra
1.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
-500
0
500
1000
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3500
4000
4500
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5500
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6500
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7500
8000
8500RX-108-1-1H
2.97
2.94
1.00
0.99
0.96
1.04
1.98
3.51
4.98
1.50
1.51
1.64
2.41
4.29
4.32
4.80
4.82
4.87
5.01
5.04
7.05
7.06
7.07
7.07
7.28
7.29
7.31
7.43
7.44
7.46
7.46
102030405060708090100110120130140150160170f1 (ppm)
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1800
1900
2000
2100
2200
2300RX-108-1-13C
15.2
4
41.6
1
76.7
377
.05
77.2
877
.37
88.2
0
128.
3612
8.69
128.
8212
9.13
129.
8113
0.04
134.
0713
4.67
168.
06
9 / 39
1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f2 (ppm)
-40
-20
0
20
40
60
80
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120
140
160
180
f1 (
ppm
)
RX-108-1-HSQC
4.204.254.304.354.404.454.504.554.604.654.704.754.804.854.904.955.005.055.105.15f2 (ppm)
60
65
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-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f2 (ppm)
0
1
2
3
4
5
6
7
8
f1 (
ppm
)
RX108-1-NOESY
{4.86,1.49}
4.624.664.704.744.784.824.864.904.944.985.025.065.10f2 (ppm)
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
2.0
2.1
2.2
2.3
2.4
2.5
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2.7
2.8
f1 (
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)
RX108-1-NOESY
{4.86,1.49}
{4.80,2.39}
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1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
0
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8000
9000
10000
RX-120-2-1H
3.01
2.99
2.00
1.00
1.02
2.93
5.00
1.05
1.63
1.65
1.73
2.37
4.58
4.61
4.62
4.64
4.90
5.05
5.07
7.19
7.19
7.20
7.21
7.23
7.25
7.28
7.31
7.32
7.32
7.33
7.34
7.34
7.35
7.36
7.38
7.41
7.42
7.42
7.42
7.43
7.44
7.44
7.44
102030405060708090100110120130140150160170f1 (ppm)
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0
100
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300
400
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800
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1300
1400
RX-120-2-13C
16.4
6
41.0
6
76.7
677
.07
77.2
277
.39
77.4
8
85.1
6
127.
3012
8.49
128.
9612
9.21
129.
6612
9.81
129.
9413
4.52
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6413
5.63
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64
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1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
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8000
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18000
19000
20000
21000RX-109-OCN3-1H
3.18
3.16
3.17
1.03
1.02
1.06
1.00
1.04
1.07
2.06
3.20
2.13
1.60
1.62
2.41
3.82
4.64
4.65
4.67
4.69
4.73
4.76
5.06
5.09
5.82
6.94
6.96
7.01
7.02
7.03
7.03
7.05
7.22
7.23
7.24
7.24
7.28
7.29
7.29
7.30
7.31
7.36
7.37
7.38
7.39
7.41
102030405060708090100110120130140150160170f1 (ppm)
-100
0
100
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400
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700
800
900
1000RX-109-OCN3-13C
16.19
40.27
55.57
76.80
77.01
77.12
77.21
77.43
110.64
120.69
121.19
128.32
128.62
129.39
129.91
130.54
134.94
158.28
167.73
13 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
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8000
9000
10000
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12000
13000CRX-120-1-1H
3.41
2.98
1.98
1.00
1.03
9.25
1.64
1.65
1.68
2.37
4.58
4.61
4.62
4.64
4.90
5.05
5.07
7.19
7.19
7.21
7.21
7.23
7.25
7.28
7.31
7.32
7.32
7.32
7.33
7.34
7.34
7.35
7.36
7.38
7.41
7.42
7.42
7.42
7.43
7.44
7.44
102030405060708090100110120130140150160170f1 (ppm)
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1400
CRX-120-1-13C
16.4
6
41.0
5
76.7
477
.06
77.2
277
.38
77.4
7
85.1
6
127.
3012
8.48
128.
9512
9.21
129.
6612
9.80
129.
9313
4.52
134.
6513
5.64
167.
64
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1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
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500
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4500
5000
5500120-6-2-1H
3.89
3.24
1.08
1.04
1.00
1.08
2.15
3.63
2.20
1.09
1.11
1.63
1.65
1.66
2.35
4.66
4.68
4.70
4.71
4.74
4.77
4.99
5.04
5.07
7.19
7.20
7.21
7.22
7.22
7.28
7.29
7.30
7.30
7.31
7.31
7.31
7.32
7.32
7.33
7.34
7.34
7.57
7.59
7.61
7.62
7.63
7.63
8.08
8.08
8.09
8.27
8.27
8.27
8.29
8.29
2030405060708090100110120130140150160170f1 (ppm)
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0
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5500
120-6-2-13C
16.2
8
40.9
6
76.7
477
.05
77.3
077
.37
77.4
1
84.6
3
124.
0612
4.52
128.
5712
9.07
129.
64
134.
6613
4.80
135.
68
148.
13
167.
72
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1.62.02.42.83.23.64.04.44.85.25.66.06.46.87.27.6f1 (ppm)
0
500
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4000
4500
RX-118-1-1H
3.02
3.00
2.05
1.00
1.06
1.98
5.22
2.16
1.63
1.64
1.76
2.35
4.58
4.60
4.62
4.64
4.92
5.04
5.06
7.18
7.18
7.20
7.27
7.29
7.30
7.31
7.32
7.33
7.34
7.39
7.41
102030405060708090100110120130140150160170180f1 (ppm)
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0
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1400RX-118-1-13C
16.4
6
40.9
9
76.7
677
.08
77.2
177
.40
85.1
3
128.
4712
8.79
128.
9112
9.62
130.
4213
2.09
134.
7013
5.66
167.
69
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1.62.02.42.83.23.64.04.44.85.25.66.06.46.87.27.6f1 (ppm)
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4000
4500
5000
5500
6000RX-118-2-1H
2.99
3.02
2.00
1.00
1.03
4.04
5.30
1.64
1.65
1.71
2.35
4.54
4.57
4.62
4.63
4.94
5.04
5.06
7.10
7.12
7.14
7.17
7.18
7.19
7.19
7.28
7.30
7.30
7.31
7.32
7.33
7.33
7.34
7.35
7.36
102030405060708090100110120130140150160170f1 (ppm)
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0
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5500RX-118-2-13C
16.5
1
41.0
1
76.7
577
.06
77.2
177
.38
85.1
6
115.
5011
5.71
128.
4512
8.88
129.
4512
9.60
130.
8513
0.94
134.
70
162.
2416
4.72
167.
69
17 / 39
1.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
-500
0
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5000
5500RX-125-1-1H
3.39
2.96
3.00
1.02
0.99
1.04
1.07
9.78
1.65
1.67
2.36
2.42
4.51
4.54
4.59
4.60
4.62
4.64
4.93
5.04
5.06
7.16
7.17
7.18
7.18
7.23
7.25
7.26
7.28
7.29
7.29
7.30
7.31
7.31
7.32
7.33
18 / 39
1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
-1000
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6000
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8000
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10000
RX-126-3-2-1H
3.17
3.02
3.00
0.99
1.05
1.60
1.06
2.13
2.10
5.48
1.65
1.66
2.36
3.86
4.50
4.53
4.59
4.61
4.93
4.95
5.03
5.06
6.94
6.96
7.17
7.18
7.19
7.29
7.29
7.30
7.31
7.31
7.41
7.43
0102030405060708090100110120130140150160170180190f1 (ppm)
-50
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50
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750
RX-126-3-2-13C
16.6
0
41.0
3
55.3
6
76.7
577
.06
77.1
677
.38
85.5
7
113.
90
128.
3812
8.76
129.
4712
9.62
130.
4013
4.82
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65
167.
69
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1.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
-2000
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0
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8000
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10000
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17000
18000
19000
20000
21000
22000
23000RX-120-5-1H
3.15
3.05
5.94
2.01
1.00
1.18
2.06
2.89
3.80
1.65
1.67
2.37
3.02
4.49
4.52
4.56
4.58
4.60
4.61
4.89
5.03
5.06
6.73
6.75
7.18
7.19
7.20
7.20
7.23
7.25
7.28
7.30
7.30
7.31
7.31
102030405060708090100110120130140150160170f1 (ppm)
-200
-100
0
100
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2200
2300
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2500RX-120-5-13C
16.6
7
40.3
941
.05
76.7
377
.05
77.1
177
.37
100.
00
111.
83
120.
51
128.
3112
8.66
129.
6913
0.06
134.
96
151.
34
167.
65
20 / 39
0102030405060708090100110120130140150160170180190200f1 (ppm)
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50
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400
450
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550
600
650
700
750YLF-31-3-13C
16.2
2
40.9
2
76.7
877
.09
77.2
077
.41
84.5
2
123.
5912
8.57
129.
0812
9.63
129.
98
134.
62
140.
58
148.
66
167.
72
21 / 39
1.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.4f1 (ppm)
0
500
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2000
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3000
3500
4000
4500
5000
Rx-120-4-1H
2.92
2.60
1.02
1.00
1.05
1.00
8.45
1.59
1.60
2.43
4.65
4.67
4.69
4.70
4.80
4.83
5.05
5.07
5.32
5.72
7.27
7.28
7.28
7.29
7.30
7.32
7.33
7.33
7.34
7.34
7.37
7.39
7.44
7.44
22 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
-1000
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6000
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8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000crx-109-1H
3.00
2.98
0.96
0.99
1.98
1.96
3.06
2.99
4.02
1.74
1.76
2.41
4.52
4.54
4.67
4.69
4.70
4.72
5.08
5.10
5.15
7.09
7.11
7.21
7.22
7.22
7.23
7.24
7.25
7.27
7.27
7.27
7.28
7.29
7.31
7.57
7.58
7.58
7.59
7.59
7.77
7.91
7.91
7.92
7.94
102030405060708090100110120130140150160170f1 (ppm)
-100
0
100
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1300
1400
1500crx-109-13C
16.7
4
41.2
4
76.8
577
.17
77.2
977
.49
77.5
3
86.2
6
125.
6412
6.63
126.
9712
7.88
128.
2112
8.36
128.
5412
8.80
129.
4912
9.67
131.
0913
2.84
134.
0113
4.73
167.
80
23 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
-200
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2200
2400
2600
2800
3000
3200
3400
3600
3800
4000
4200ZC-21-1-1H
3.09
3.05
1.01
1.03
1.08
1.00
1.01
1.06
5.38
1.10
1.58
1.60
2.45
4.53
4.56
4.65
4.67
4.68
4.70
5.07
5.10
5.36
7.06
7.07
7.07
7.08
7.14
7.14
7.15
7.15
7.27
7.27
7.28
7.29
7.33
7.34
7.34
7.45
7.46
0102030405060708090100110120130140150160170180f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550CZ-21-1-13C
15.92
30.95
40.69
76.76
77.08
77.40
77.54
77.79
81.01
126.19
128.34
128.43
128.82
129.58
129.82
134.74
135.73
166.93
24 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
cz-21-2-1H-2
2.71
3.00
1.86
0.93
0.99
1.86
4.90
1.00
0.98
0.98
1.62
1.63
1.67
2.36
2.38
4.66
4.68
4.68
4.95
5.05
5.07
7.20
7.21
7.22
7.23
7.29
7.31
7.33
7.34
7.34
7.34
7.36
7.36
7.38
7.68
7.69
7.69
7.70
7.71
7.71
8.50
8.51
8.68
8.69
8.69
8.70
102030405060708090100110120130140150160170180190200f1 (ppm)
0
500
1000
1500
2000
2500
3000
3500
4000
4500
cz-21-2-13C-2
16.2
8
40.9
5
76.7
277
.04
77.3
577
.44
83.5
4
123.
5612
8.55
129.
0312
9.63
134.
6213
6.41
150.
3915
1.05
167.
68
25 / 39
26 / 39
27 / 39
2030405060708090100110120130140150160170180f1 (ppm)
-100
0
100
200
300
400
500
600
700
800
900
1000Rx-121-13C
16.4
6
57.1
1
76.8
177
.13
77.3
477
.40
77.4
577
.49
84.1
4
127.
3812
7.58
128.
2412
8.32
128.
4212
8.52
128.
6712
8.79
128.
8412
8.87
129.
3612
9.66
129.
8612
9.88
130.
1313
3.84
134.
7213
5.87
167.
82
28 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000CZ-23-1-1H
3.14
2.99
1.01
1.00
1.93
1.01
0.94
14.1
7
1.52
1.53
2.45
3.51
3.54
3.67
3.70
4.52
4.54
4.58
4.60
5.07
5.10
5.13
7.18
7.19
7.20
7.21
7.23
7.25
7.25
7.27
7.29
7.30
7.30
7.31
7.32
7.32
7.35
102030405060708090100110120130140150160170180f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
CZ-23-1-13C
16.4
3
21.3
9
57.0
7
76.7
877
.09
77.3
777
.41
83.9
7
127.
5112
8.27
128.
3712
8.79
129.
2412
9.33
129.
6613
0.78
134.
8313
5.98
139.
79
167.
76
29 / 39
102030405060708090100110120130140150160170180f1 (ppm)
-200
0
200
400
600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200RX-128-1-13C
16.2
7
57.0
8
76.7
377
.05
77.3
677
.46
83.1
8
127.
6912
8.26
128.
3712
8.46
128.
5312
8.74
128.
8512
8.90
129.
0212
9.61
129.
8213
0.57
132.
3313
4.69
135.
4213
5.71
167.
80
30 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500RX-126-2-1H
2.97
1.01
0.98
1.00
1.00
1.08
1.00
2.01
10.37
1.08
1.53
1.55
3.55
3.58
3.86
3.89
4.49
4.51
4.66
4.68
5.07
5.10
5.43
7.09
7.10
7.10
7.24
7.26
7.27
7.28
7.29
7.29
7.29
7.30
7.30
7.31
7.32
7.34
7.49
7.50
7.51
0102030405060708090100110120130140150160170180f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700RX-126-2-13C
15.87
57.08
76.74
77.06
77.38
77.84
77.96
79.20
126.17
127.78
128.41
128.45
128.54
128.82
128.90
129.57
130.00
134.69
135.16
135.91
167.01
31 / 39
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.0f1 (ppm)
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000RX-132-1H
3.18
2.23
3.12
0.99
1.00
1.00
1.04
2.02
3.25
5.14
1.11
1.12
1.14
2.06
2.07
2.08
2.09
2.10
2.11
2.12
2.13
2.17
2.19
2.21
2.22
2.23
2.39
4.35
4.36
4.37
4.38
4.42
4.44
4.96
5.05
5.07
7.10
7.11
7.12
7.12
7.26
7.27
7.28
7.28
7.30
7.31
7.32
7.41
7.42
7.43
7.44
7.45
7.46
7.47
0102030405060708090100110120130140150160170180190f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
RX-132-13C
10.3
2
24.0
8
41.2
4
76.7
677
.08
77.4
082
.20
86.3
6
128.
3612
8.58
128.
7712
9.20
129.
6412
9.83
133.
8513
4.70
167.
45
32 / 39
2.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6500
7000
7500
8000
8500
CjZ-46-1-1H
3.05
1.03
2.10
1.00
2.21
3.40
8.99
2.15
2.44
2.49
4.42
4.44
5.16
5.18
5.58
7.14
7.16
7.30
7.31
7.33
7.34
7.43
7.45
7.47
7.49
7.51
7.66
7.67
2030405060708090100110120130140150160170180f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700CjZ-46-1-13C
41.36
76.88
77.20
77.52
77.72
82.42
86.90
127.74
128.41
128.49
128.54
128.60
128.74
128.86
128.96
129.32
129.74
129.94
130.04
133.84
134.58
136.21
165.68
33 / 39
30405060708090100110120130140150160170180f1 (ppm)
-100
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300x-132-2-13C
41.6
5
76.7
377
.04
77.3
677
.73
86.8
887
.39
128.
2812
8.42
129.
0112
9.79
130.
6613
2.74
134.
04
160.
72
34 / 39
2.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
22000
23000
24000RX-132-2-2-1H
3.11
1.03
1.00
1.16
2.14
5.17
3.44
2.52
4.53
4.55
4.95
5.07
5.09
7.16
7.18
7.28
7.33
7.33
7.34
7.35
7.37
7.37
7.39
7.45
7.46
7.48
7.50
7.51
7.51
2030405060708090100110120130140150160170180190f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700
750RX-132-2-2-13C
41.3
7
76.7
977
.11
77.3
077
.43
86.5
7
106.
53
128.
3712
8.51
128.
6112
8.74
129.
0012
9.32
130.
1113
0.72
131.
4413
4.01
158.
53
35 / 39
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
ylf-31-1-1H
3.00
2.92
2.94
1.13
0.96
1.00
1.97
3.16
4.84
1.51
1.71
2.35
4.40
4.42
4.89
4.98
5.01
7.11
7.11
7.12
7.13
7.28
7.29
7.30
7.32
7.33
7.38
7.40
7.41
7.42
7.43
7.45
7.47
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
ylf-31-1-13C
23.93
24.05
41.33
76.77
77.09
77.13
77.40
81.83
128.37
128.60
128.83
129.14
129.81
129.89
133.92
134.73
170.58
36 / 39
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
45000
50000
55000
60000
65000ylf-41-1H
3.03
3.00
3.00
0.98
0.99
4.97
1.61
1.63
2.41
3.57
4.57
4.58
4.60
4.62
5.19
7.43
0102030405060708090100110120130140150160170180190200f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700
750ylf-41-13C
16.4
1
40.9
8
62.9
1
76.7
677
.08
77.1
977
.40
84.7
7
128.
5112
9.10
129.
7813
3.46
167.
44
37 / 39
2.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
-2000
0
2000
4000
6000
8000
10000
12000
14000
16000
18000
20000
22000
24000
26000
28000
30000
32000
34000
36000CJZ-52-16-1H
3.00
2.83
0.94
0.95
0.93
0.91
1.86
4.67
4.09
2.78
2.19
2.51
4.67
4.70
5.13
5.16
5.59
5.99
7.23
7.24
7.25
7.25
7.28
7.30
7.31
7.32
7.32
7.33
7.34
7.34
7.36
7.36
7.41
7.43
7.44
7.45
7.45
7.46
7.46
7.47
7.47
7.48
7.59
7.60
7.61
7.62
38 / 39
5 X-Ray diffraction of (3R,6S)-4-(benzyloxy)-2-methyl-6-phenyl-3-(p-tolyl)-1,2,4- oxadiazinan-5–one
39 / 39
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