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  • Supporting Information

    N-Heterocyclic Carbene-Catalyzed [3+2] Annulation of Bromoenals with

    3-Aminooxindoles: Highly Enantioselective Synthesis of Spirocyclic

    Oxindolo-γ-Lactams

    Kun-Quan Chen,a,b Yao Li,a,b Chun-Lin Zhang,a De-Qun Sun*b and Song Ye*a

    a Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular

    Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing

    100190, China. E-mail: songye@iccas.ac.cn

    b Marine College, Shandong University at Weihai, 180 Wenhua West Road, Weihai 264209,

    China.. E-mail: dequn.sun@sdu.edu.cn.

    Table of Contents

    Part I NMR Spectra ................................................................................................. 1 

    Part II HPLC Spectra ............................................................................................ 20 

    Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2016

  •  

    1   

    Part I NMR Spectra

    3a

    9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

    1. 09 19

    2. 77 93

    2. 79 42

    2. 81 20

    2. 82 70

    3. 67 17

    3. 69 98

    3. 70 37

    3. 73 24

    3. 81 45

    3. 82 95

    3. 84 24

    3. 85 74

    4. 08 81

    4. 11 99

    5. 00 44

    5. 03 62

    6. 38 41

    6. 39 78

    6. 41 15

    6. 92 28

    6. 93 80

    7. 06 38

    7. 07 85

    7. 09 38

    7. 13 59

    7. 15 07

    7. 16 07

    7. 16 47

    7. 17 56

    7. 19 11

    7. 19 51

    7. 28 87

    7. 30 35

    7. 31 82

    7. 42 08

    7. 43 49

    8. 99

    1. 00

    1. 02

    1. 01

    1. 01

    1. 00

    2. 97

    2. 12

    2. 17

    5. 10

    1. 01

    1. 02

    NAME n-3+2-1 EXPNO 9 PROCNO 1 Date_ 20150428 Time 8.24 INSTRUM spect PROBHD 5 mm CPPBBO BB PULPROG zg30 TD 65536 SOLVENT CDCl3 NS 16 DS 2 SWH 10000.000 Hz FIDRES 0.152588 Hz AQ 3.2768500 sec RG 31.72 DW 50.000 usec DE 6.50 usec TE 298.0 K D1 1.00000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 500.1330885 MHz NUC1 1H P1 10.60 usec SI 65536 SF 500.1300121 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 1.00

    ckq-290

    210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

    27 .5

    5

    35 .1

    5

    44 .0

    8 49

    .0 1

    71 .7

    2

    83 .8

    6

    10 9.

    66

    12 2.

    16 12

    3. 26

    12 6.

    64 12

    7. 35

    12 8.

    52 12

    8. 61

    12 8.

    72 12

    8. 75

    12 9.

    89 13

    2. 67

    13 4.

    75 14

    3. 49

    14 8.

    08

    17 3.

    56 17

    4. 04

    NAME n-3+2-1 EXPNO 10 PROCNO 1 Date_ 20150428 Time 8.26 INSTRUM spect PROBHD 5 mm CPPBBO BB PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 88 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010548 sec RG 192.89 DW 16.800 usec DE 18.00 usec TE 298.0 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 125.7703637 MHz NUC1 13C P1 9.80 usec SI 32768 SF 125.7577763 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.40

    ckq-290

  •  

    2   

    N H

    O

    N

    O

    Ph Boc

    3b

    9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm

    1. 15 16

    2. 73 31

    2. 75 17

    2. 77 40

    2. 79 26

    3. 55 44

    3. 58 93

    3. 63 01

    3. 71 63

    3. 73 50

    3. 75 10

    3. 76 95

    6. 64 54

    6. 66 46

    6. 86 12

    6. 88 01

    7. 13 06

    7. 14 87

    7. 16 73

    7. 17 85

    7. 18 38

    7. 20 64

    7. 22 46

    7. 24 28

    7. 26 21

    7. 27 81

    7. 29 74

    7. 38 03

    7. 39 87

    8. 63

    1. 00

    1. 05

    1. 03

    1. 09

    1. 94

    6. 65

    1. 02

    NAME n-3+2-2 EXPNO 59 PROCNO 1 Date_ 20150508 Time 8.03 INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 8012.820 Hz FIDRES 0.244532 Hz AQ 2.0447731 sec RG 206.33 DW 62.400 usec DE 6.50 usec TE 298.8 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 400.2424716 MHz NUC1 1H P1 14.80 usec SI 65536 SF 400.2400088 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 1.00

    ckq-311

    210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

    27 .5

    4

    34 .9

    1

    49 .1

    5

    72 .0

    2

    84 .2

    2

    11 0.

    11

    12 2.

    54 12

    3. 32

    12 8.

    23 12

    8. 42

    12 8.

    47 12

    9. 05

    12 9.

    88 13

    2. 53

    14 0.

    98

    14 8.

    20

    17 3.

    51 17

    5. 31NAME n-3+2-2

    EXPNO 60 PROCNO 1 Date_ 20150508 Time 8.08 INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 263 DS 4 SWH 24038.461 Hz FIDRES 0.366798 Hz AQ 1.3631988 sec RG 206.33 DW 20.800 usec DE 6.50 usec TE 299.9 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 100.6504916 MHz NUC1 13C P1 10.00 usec SI 32768 SF 100.6404141 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.40

    ckq-311

  •  

    3   

    3c

    9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

    1. 09 06

    2. 71 51

    2. 73 89

    2. 75 32

    2. 77 11

    2. 78 53

    3. 59 24

    3. 62 03

    3. 65 22

    3. 69 17

    3. 70 59

    3. 71 94

    3. 73 36

    6. 58 72

    6. 60 27

    6. 81 20

    6. 82 70

    7. 10 68

    7. 12 14

    7. 13 66

    7. 16 23

    7. 17 10

    7. 17 70

    7. 18 51

    7. 19 16

    7. 26 66

    7. 31 61

    7. 33 13

    7. 34 65

    7. 38 56

    7. 40 02

    9. 16

    4. 17

    2. 12

    1. 00

    1. 99

    4. 34

    1. 11

    1. 11

    NAME n-3+2-1 EXPNO 7 PROCNO 1 Date_ 20150428 Time 8.06 INSTRUM spect PROBHD 5 mm CPPBBO BB PULPROG zg30 TD 65536 SOLVENT CDCl3 NS 16 DS 2 SWH 10000.000 Hz FIDRES 0.152588 Hz AQ 3.2768500 sec RG 31.72 DW 50.000 usec DE 6.50 usec TE 298.0 K D1 1.00000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 500.1330885 MHz NUC1 1H P1 10.60 usec SI 65536 SF 500.1300107 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 1.00

    ckq-305

    210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

    25 .6

    9 27

    .5 0

    34 .8

    4

    49 .1

    9

    72 .0

    6

    83 .7

    6

    10 8.

    24

    12 1.

    97 12

    3. 20

    12 8.

    04 12

    8. 11

    12 8.

    19 12

    8. 35

    12 8.

    65 12

    9. 85

    13 2.

    47

    14 3.

    83 14

    8. 05

    17 3.

    69

    NAME n-3+2-1 EXPNO 8 PROCNO 1 Date_ 20150428 Time 8.10 INSTRUM spect PROBHD 5 mm CPPBBO BB PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 245 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010548 sec RG 192.89 DW 16.800 usec DE 18.00 usec TE 298.0 K D1