Post on 08-Jul-2018
Organocatalytic asymmetric direct vinylogous Michael addition of α,β- unsaturated γ-butyrolactam to nitroolefins
Abhijnan Ray Choudhury and Santanu Mukherjee*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, INDIA
sm@orgchem.iisc.ernet.in
SUPPORTING INFORMATION: PART B
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-2
10 9 8 7 6 5 4 3 2 1 0 ppm
4.00
14.
006
6.09
06.
095
6.09
8
7.10
87.
112
8.17
4
2.11
0
0.92
9
0.94
9
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
49.0
89
76.8
4577
.164
77.4
82
127.
592
146.
099
175.
679
NH
O
NH
O
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-3
10 9 8 7 6 5 4 3 2 1 0 ppm
1.53
0
4.32
7
6.12
46.
128
6.13
56.
140
7.16
47.
169
7.17
57.
180
9.32
5
2.04
9
0.96
4
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.0
04
51.5
72
76.6
8677
.004
77.3
2282
.894
127.
827
145.
114
149.
473
169.
094
\
N O
Boc1
N O
Boc1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-4
10 9 8 7 6 5 4 3 2 1 0 ppm
0.87
40.
887
1.27
01.
289
1.30
61.
351
1.37
61.
693
2.03
72.
244
2.27
12.
300
2.34
12.
669
2.83
82.
865
2.89
23.
050
3.39
63.
414
3.79
73.
815
4.98
15.
006
5.04
95.
370
6.01
36.
058
6.07
8
7.03
87.
301
7.42
57.
569
7.58
07.
886
7.90
9
8.61
08.
620
1.19
6
2.12
3
1.05
1
0.90
0
1.78
6
0.83
30.
998
0.87
7
0.81
3
1.78
8
1.89
2
2.03
10.
885
1.12
51.
026
0.91
5
1.00
0
N
HN
OH
OH
III
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-5
10 9 8 7 6 5 4 3 2 1 0 ppm
1.00
01.
017
1.12
41.
248
1.48
01.
504
1.52
41.
754
2.00
72.
031
2.03
62.
043
2.06
32.
079
2.09
52.
220
2.24
12.
754
2.76
42.
785
2.87
52.
900
2.90
82.
933
3.04
63.
056
3.34
73.
366
3.71
03.
726
5.01
95.
027
5.05
75.
608
5.61
75.
998
6.02
37.
137
7.14
37.
265
7.27
17.
277
7.29
47.
300
7.49
97.
511
7.91
47.
937
8.58
08.
591
5.86
21.
016
1.27
12.
214
1.02
42.
139
0.94
8
1.17
82.
053
1.03
21.
043
1.93
2
1.91
3
0.91
4
0.94
2
1.06
90.
895
1.00
7
1.01
1
1.00
0
200 180 160 140 120 100 80 60 40 20 0 ppm
19.2
2821
.063
26.2
2228
.171
39.8
86
49.5
4150
.088
59.6
2571
.667
74.5
8676
.682
77.0
0077
.318
101.
776
114.
600
118.
412
121.
850
121.
855
126.
545
131.
335
140.
389
143.
944
147.
311
147.
408
157.
284
N
HN
OH
OIV
N
HN
OH
OIV
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-6
10 9 8 7 6 5 4 3 2 1 0 ppm
0.82
20.
840
0.85
80.
963
0.97
60.
996
1.01
81.
029
1.34
01.
359
1.37
71.
408
1.42
51.
642
1.93
61.
961
1.99
12.
664
2.67
42.
696
2.71
72.
787
2.81
42.
838
2.84
62.
871
2.92
82.
943
2.94
82.
964
3.09
23.
111
3.12
33.
143
3.76
25.
264
5.57
85.
585
7.12
17.
187
7.19
27.
210
7.21
57.
260
7.47
27.
483
7.84
27.
864
8.45
98.
470
3.23
81.
073
4.05
71.
055
0.99
8
1.09
72.
024
0.97
81.
031
3.18
1
1.25
2
1.02
40.
977
0.98
1
1.00
2
1.00
0
N
HN
OH
OMeV
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-7
10 9 8 7 6 5 4 3 2 1 0 ppm
0.92
60.
942
1.24
81.
515
1.54
81.
562
1.57
81.
672
1.86
11.
940
1.96
21.
995
2.25
52.
275
2.29
52.
315
2.66
12.
704
2.72
62.
896
2.91
73.
333
3.95
95.
093
5.12
45.
136
5.14
95.
985
6.00
46.
011
6.02
96.
046
6.05
46.
072
7.26
37.
339
7.39
17.
397
7.41
47.
420
7.45
48.
037
8.06
08.
789
8.80
0
1.09
0
2.48
91.
134
1.09
81.
172
1.14
8
4.83
21.
975
0.94
3
3.31
5
2.01
1
1.07
0
3.12
0
1.07
3
1.00
0
N
HN
OMs
OMe
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-8
10 9 8 7 6 5 4 3 2 1 0 ppm
1.09
01.
104
1.12
41.
145
1.15
71.
352
1.37
51.
405
1.71
01.
729
1.74
71.
809
2.47
42.
489
3.18
53.
206
3.22
83.
274
3.30
13.
321
3.37
13.
394
3.41
53.
476
3.93
35.
168
5.19
35.
229
5.29
05.
348
5.37
25.
807
5.82
15.
833
5.84
95.
865
5.87
65.
891
7.26
07.
348
7.35
37.
371
7.37
67.
487
7.49
77.
572
7.99
88.
021
8.72
98.
739
1.25
71.
979
3.12
1
0.87
4
4.78
8
3.05
5
1.82
71.
121
0.86
2
1.09
60.
939
0.92
1
1.02
8
1.00
0
N
HN
OH
OMe
VI
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-9
10 9 8 7 6 5 4 3 2 1 0 ppm
1.26
71.
283
1.29
91.
623
1.64
41.
656
1.67
51.
693
1.71
01.
730
1.80
21.
819
1.83
41.
851
2.21
32.
225
2.77
82.
812
2.97
02.
992
3.02
23.
043
3.09
03.
111
3.14
33.
725
3.74
13.
758
5.93
2
7.26
47.
281
7.28
87.
304
7.31
07.
590
7.60
17.
656
7.66
17.
937
7.96
08.
683
8.69
4
9.39
1
3.00
01.
024
1.09
23.
197
1.26
81.
068
0.96
81.
195
0.98
5
1.88
5
0.97
4
1.25
21.
074
0.92
71.
404
1.16
3
1.27
4
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
7.19
4
22.5
2622
.901
27.3
0732
.662
45.7
9450
.081
53.5
3956
.379
72.3
1176
.685
77.0
0277
.320
104.
937
118.
693
122.
325
126.
508
131.
446
140.
723
143.
115
146.
703
156.
671
N
HN
O
OHVII
N
HN
O
OHVII
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-10
10 9 8 7 6 5 4 3 2 1 0 ppm
1.22
01.
236
1.25
01.
442
1.45
71.
489
1.50
51.
594
1.61
11.
631
1.70
31.
720
1.73
41.
751
2.09
12.
102
2.11
22.
564
2.59
82.
611
2.92
82.
948
3.43
73.
837
3.85
33.
940
5.87
2
7.12
87.
263
7.31
07.
333
7.67
67.
686
7.94
07.
950
7.96
47.
982
8.00
58.
728
8.73
9
3.00
01.
195
1.24
63.
022
1.19
21.
056
1.02
4
1.94
2
1.15
7
1.22
03.
139
0.97
6
1.16
31.
462
0.92
6
1.09
8
0.91
3
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
7.34
4
23.6
8924
.453
27.4
2032
.925
46.8
4754
.902
55.8
5056
.181
73.2
5676
.683
77.0
0177
.247
77.3
19
100.
690
119.
375
121.
416
126.
520
131.
820
143.
208
144.
096
147.
717
157.
837
N
HN
O
OMeVIII
N
HN
O
OMeVIII
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-11
10 9 8 7 6 5 4 3 2 1 0 ppm
1.60
2
7.26
48.
078
8.08
38.
086
8.09
08.
094
8.09
88.
101
8.33
28.
340
8.34
8
2.05
22.
000
N
N
Cl
Cl
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-12
10 9 8 7 6 5 4 3 2 1 0 ppm
1.23
71.
255
1.27
31.
510
1.53
11.
543
1.80
72.
055
2.08
12.
112
2.20
02.
220
2.66
72.
678
2.68
92.
700
2.72
32.
803
2.83
62.
861
2.92
12.
941
3.39
43.
410
3.90
14.
954
4.98
75.
935
7.02
17.
035
7.34
37.
348
7.36
67.
371
7.40
97.
420
7.53
17.
535
7.91
97.
927
7.93
47.
941
7.97
57.
998
8.33
08.
338
8.34
48.
352
8.62
98.
640
1.82
46.
318
1.91
34.
432
2.02
9
2.43
64.
127
2.11
5
2.11
5
5.61
2
3.53
1
1.78
4
1.60
72.
292
1.81
72.
073
2.05
32.
140
1.94
5
2.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
23.2
3626
.492
27.7
62
39.6
70
49.4
7549
.836
55.6
3660
.080
76.1
4976
.682
77.0
0077
.317
101.
992
114.
630
118.
273
121.
848
122.
426
123.
010
127.
260
131.
542
132.
125
140.
336
144.
664
144.
875
147.
350
156.
384
157.
643
N
HN
O
OMe
R' =OR'
OR'
N
N
IX
N
HN
O
OMe
R' =OR'
OR'
N
N
IX
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-13
10 9 8 7 6 5 4 3 2 1 ppm
0.77
31.
151
1.15
71.
168
1.17
51.
186
1.19
31.
351
1.37
01.
681
1.71
82.
292
2.32
52.
542
2.56
82.
592
2.95
62.
982
2.98
93.
014
3.44
33.
476
3.51
03.
831
5.26
95.
505
7.20
27.
229
7.23
47.
260
7.44
07.
451
7.83
67.
858
8.42
18.
432
3.06
8
2.03
33.
240
3.04
3
1.02
41.
067
2.07
2
1.00
4
2.96
8
1.06
6
1.90
60.
990
1.00
4
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
11.9
80
21.0
3925
.352
27.5
7328
.104
37.3
61
43.2
68
55.6
3758
.485
59.6
89
71.5
1476
.683
77.0
0177
.318
101.
381
118.
458
121.
234
126.
517
131.
124
143.
844
147.
244
148.
382
157.
556
NH
OHN
OMe
NH
OHN
OMe
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-14
10 9 8 7 6 5 4 3 2 1 0 ppm
1.27
41.
347
1.37
51.
405
1.53
31.
561
1.58
71.
813
1.89
51.
912
1.94
22.
453
2.45
82.
486
2.75
12.
764
2.78
22.
793
2.85
42.
986
3.13
13.
157
3.19
03.
307
3.31
03.
777
3.79
93.
804
3.82
53.
831
4.93
85.
591
7.27
97.
283
7.31
87.
341
7.62
77.
638
7.88
67.
909
8.58
48.
595
3.00
0
2.07
11.
468
2.19
71.
022
2.01
4
0.96
0
1.02
8
1.88
9
0.93
5
0.89
2
0.87
30.
967
0.92
40.
930
0.97
7
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
12.1
8620
.869
26.5
5128
.169
28.3
3038
.128
44.4
8248
.363
48.5
7748
.789
49.0
0149
.214
49.4
2849
.641
59.0
1460
.890
71.5
20
105.
096
119.
853
123.
514
128.
299
131.
466
143.
876
147.
323
149.
157
158.
298
NH
OHN
OH
NH
OHN
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-15
10 9 8 7 6 5 4 3 2 1 0 ppm
0.75
30.
771
0.78
91.
048
1.17
31.
192
1.21
01.
238
1.25
11.
630
1.66
31.
701
1.90
41.
915
1.96
11.
982
1.99
02.
012
2.09
12.
530
2.55
42.
571
2.58
92.
926
2.93
73.
181
3.20
33.
225
3.28
33.
311
3.34
23.
503
3.52
63.
608
3.63
04.
211
5.28
56.
075
6.88
17.
038
7.04
37.
061
7.06
67.
261
7.56
07.
571
7.66
97.
692
8.57
18.
582
3.00
09.
187
3.85
5
1.89
90.
987
0.94
60.
888
1.06
8
0.94
30.
995
0.97
91.
010
1.22
6
0.90
4
0.91
9
0.95
70.
969
0.97
60.
954
0.97
2
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
11.5
65
24.7
6426
.707
27.0
6831
.802
36.0
6943
.822
46.0
54
57.3
1958
.632
59.9
17
76.6
8477
.001
77.3
1978
.354
100.
394
118.
556
122.
152
125.
475
131.
079
143.
463
145.
033
146.
837
157.
743
NH
OHN
O
XII
NH
OHN
O
XII
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-16
10 9 8 7 6 5 4 3 2 1 0 ppm
1.65
7
4.50
04.
521
4.64
24.
651
4.67
74.
704
4.72
84.
877
4.88
26.
175
6.17
96.
191
6.19
47.
022
7.02
77.
037
7.04
27.
255
7.26
07.
272
7.33
47.
353
7.37
17.
394
7.41
37.
430
9.15
5
1.05
52.
116
1.05
8
1.00
0
1.07
9
4.85
2
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.1
33
43.8
32
65.1
1573
.277
76.6
8477
.002
77.3
1984
.338
127.
677
128.
600
128.
763
129.
378
134.
839
146.
163
149.
362
168.
275
NO2
NH
OBoc
3a
NO2
NH
OBoc
3a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-17
NO2
NH
OBoc
rac-3a
NO2
NH
OBoc
3a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-18
NO2
NH
OBoc
ent-3a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-19
10 9 8 7 6 5 4 3 2 1 0 ppm
1.64
3
2.33
4
4.45
64.
466
4.48
74.
497
4.58
14.
591
4.60
54.
615
4.62
44.
639
4.66
44.
669
4.69
34.
840
4.84
46.
149
6.15
26.
164
6.16
77.
024
7.02
87.
040
7.04
37.
122
7.14
27.
186
7.20
57.
263
9.04
1
3.11
1
1.05
12.
160
1.05
2
1.00
0
1.08
82.
209
2.10
7
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20.9
61
28.0
34
43.4
67
65.1
4673
.361
76.6
8277
.000
77.3
1984
.128
127.
472
128.
544
129.
922
131.
633
138.
344
146.
331
149.
218
168.
273
NO2
NH
OBoc
Me
3b
NO2
NH
OBoc
Me
3b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-20
NO2
NH
OBoc
Me
rac-3b
NO2
NH
OBoc
Me
3b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-21
NO2
NH
OBoc
Me
ent-3b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-22
10 9 8 7 6 5 4 3 2 1 0 ppm
1.64
5
4.52
14.
529
4.54
94.
556
4.59
84.
606
4.62
24.
630
4.64
04.
668
4.69
24.
856
4.86
06.
170
6.17
46.
186
6.18
97.
009
7.01
47.
025
7.02
97.
080
7.10
17.
123
7.22
37.
236
7.24
57.
260
9.02
9
0.96
42.
093
1.06
2
1.00
0
1.05
82.
134
1.98
8
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.0
68
43.3
02
64.8
7573
.573
76.6
7576
.993
77.3
1184
.376
116.
266
116.
482
128.
852
129.
355
129.
439
130.
456
130.
489
145.
971
149.
406
161.
257
163.
728
168.
042
NO2
NH
OBoc
F
3c
NO2
NH
OBoc
F
3c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-23
NO2
NH
OBoc
F
rac-3c
NO2
NH
OBoc
F
3c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-24
10 9 8 7 6 5 4 3 2 1 0 ppm
1.63
1
4.51
24.
522
4.54
24.
552
4.58
34.
591
4.60
64.
615
4.62
34.
637
4.66
64.
689
4.84
46.
159
6.16
26.
174
6.17
76.
993
6.99
77.
008
7.01
27.
184
7.20
47.
260
7.36
37.
383
9.14
5
1.02
12.
253
1.08
4
1.00
0
1.10
32.
260
2.28
4
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.0
6029
.619
43.3
93
64.7
4373
.350
76.6
8277
.000
77.3
1884
.406
129.
022
129.
528
133.
218
134.
548
145.
879
149.
382
167.
983
NO2
NH
OBoc
Cl
3d
NO2
NH
OBoc
Cl
3d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-25
NO2
NH
OBoc
Cl
rac-3d
NO2
NH
OBoc
Cl
3d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-26
10 9 8 7 6 5 4 3 2 1 0 ppm
1.63
5
4.50
84.
519
4.53
84.
549
4.57
14.
580
4.59
44.
604
4.61
34.
635
4.65
84.
665
4.68
84.
845
6.16
36.
166
6.17
86.
181
6.99
16.
995
7.00
77.
010
7.12
77.
147
7.26
37.
521
7.54
2
9.01
5
0.94
42.
072
1.02
9
0.98
6
1.00
02.
213
2.04
5
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.0
74
43.4
64
64.6
6573
.277
76.6
9677
.014
77.3
3284
.431
122.
651
128.
923
129.
339
132.
497
133.
753
145.
871
149.
411
167.
966
NO2
NH
OBoc
Br
3e
NO2
NH
OBoc
Br
3e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-27
NO2
NH
OBoc
Br
rac-3e
NO2
NH
OBoc
Br
3e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-28
NO2
NH
OBoc
Br
ent-3e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-29
10 9 8 7 6 5 4 3 2 1 0 ppm
1.65
5
3.81
2
6.16
86.
183
6.75
26.
796
6.82
36.
846
6.86
76.
914
6.93
56.
960
7.03
57.
039
7.05
17.
055
7.10
47.
126
7.16
57.
186
7.23
87.
264
7.27
6
8.28
5
3.05
1
1.00
01.
911
0.98
8
0.91
4
2.19
71.
057
2.63
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.1
44
43.3
13
55.3
23
65.2
3273
.707
76.6
8377
.000
77.3
1884
.266
114.
733
126.
521
128.
678
128.
843
146.
382
149.
442
159.
612
168.
232
NO2
NH
OBoc
OMe
3f
NO2
NH
OBoc
OMe
3f
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-30
NO2
NH
OBoc
OMe
rac-3f
NO2
NH
OBoc
OMe
3f
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-31
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
1.64
4
4.51
24.
522
4.54
24.
552
4.59
74.
607
4.62
14.
631
4.63
94.
651
4.68
14.
705
4.86
44.
868
6.18
66.
189
6.20
16.
204
7.01
67.
020
7.03
17.
035
7.13
97.
148
7.15
67.
174
7.32
47.
337
7.34
87.
351
9.23
5
1.00
92.
137
1.05
2
1.00
0
1.15
21.
640
2.35
6
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.0
78
43.5
25
64.7
0973
.137
76.6
8277
.000
77.3
1884
.467
125.
699
128.
034
128.
860
128.
981
130.
592
135.
263
136.
850
145.
790
149.
416
167.
902
NO2
NH
OBoc
Cl
3g
NO2
NH
OBoc
Cl
3g
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-32
NO2
NH
OBoc
Cl
rac-3g
NO2
NH
OBoc
Cl
3g
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-33
NO2
NH
OBoc
Cl
ent-3g
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-34
10 9 8 7 6 5 4 3 2 1 0 ppm
1.61
9
4.68
14.
694
4.70
24.
710
5.04
45.
048
5.05
95.
073
5.08
15.
095
6.10
36.
106
6.11
96.
947
6.95
16.
962
6.96
77.
055
7.07
67.
260
7.27
67.
282
7.29
87.
303
7.46
57.
470
9.12
5
1.98
8
2.03
4
1.00
0
1.02
81.
029
1.03
30.
966
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.1
02
40.4
24
62.0
29
73.7
5676
.676
76.9
9477
.312
84.5
80
127.
778
128.
608
128.
697
130.
529
130.
640
135.
149
135.
529
146.
348
149.
681
168.
166
NO2
NH
OBoc
Cl
Cl
3h
NO2
NH
OBoc
Cl
Cl
3h
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-35
NO2
NH
OBoc
Cl
Cl
rac-3h
NO2
NH
OBoc
Cl
Cl
3h
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-36
10 9 8 7 6 5 4 3 2 1 0 ppm
1.68
4
4.55
54.
580
4.60
04.
624
4.79
84.
822
4.84
24.
866
4.97
06.
177
6.18
16.
193
6.19
67.
050
7.05
47.
065
7.06
97.
260
7.37
47.
395
7.51
67.
527
7.53
67.
539
7.69
87.
815
7.82
87.
838
7.84
57.
860
7.88
67.
908
9.10
8
1.08
62.
118
1.09
1
1.00
0
1.10
31.
166
2.37
31.
171
2.25
81.
160
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.1
29
43.8
30
65.0
7173
.252
76.6
9577
.012
77.3
3084
.339
125.
280
126.
565
126.
733
126.
869
127.
711
127.
804
128.
761
129.
344
132.
255
132.
944
133.
217
146.
179
149.
401
168.
158
NO2
NH
OBoc
3i
NO2
NH
OBoc
3i
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-37
NO2
NH
OBoc
rac-3i
NO2
NH
OBoc
3i
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-38
10 9 8 7 6 5 4 3 2 1 0 ppm
1.60
8
4.30
84.
319
4.34
14.
352
4.50
84.
532
4.54
14.
566
4.72
34.
733
4.74
54.
757
4.76
84.
956
4.96
04.
965
6.19
66.
199
6.21
16.
214
6.29
66.
304
6.36
46.
368
6.37
67.
178
7.18
27.
193
7.19
77.
260
7.42
5
9.06
7
1.02
91.
100
1.05
11.
002
1.05
11.
060
1.02
9
1.00
00.
980
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
27.9
98
38.1
32
63.4
01
72.5
3476
.670
76.9
8877
.305
84.3
27
108.
853
110.
748
128.
634
143.
178
146.
843
148.
872
149.
076
168.
136
NO2
NH
OBoc
O
3j
NO2
NH
OBoc
O
3j
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-39
NO2
NH
OBoc
O
rac-3j
NO2
NH
OBoc
O
3j
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-40
NO2
NH
OBoc
O
ent-3j
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-41
10 9 8 7 6 5 4 3 2 1 0 ppm
1.64
7
4.48
74.
500
4.52
14.
533
4.55
74.
580
4.59
14.
614
4.89
64.
906
4.91
84.
929
4.94
14.
961
4.96
64.
970
6.20
26.
209
6.21
76.
225
6.98
56.
993
7.01
67.
018
7.03
07.
040
7.16
07.
164
7.17
67.
180
7.27
07.
313
7.32
5
9.07
3
1.00
01.
015
1.10
91.
031
0.97
3
0.99
31.
020
1.06
80.
975
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.0
95
39.8
70
64.8
8374
.973
76.6
8277
.000
77.3
1884
.454
125.
762
126.
344
127.
437
128.
974
137.
296
146.
312
149.
254
168.
110
NO2
NH
OBoc
S
3k
NO2
NH
OBoc
S
3k
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-42
NO2
NH
OBoc
S
rac-3k
NO2
NH
OBoc
S
3k
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-43
NO2
NH
OBoc
S
ent-3k
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-44
10 9 8 7 6 5 4 3 2 1 0 ppm
1.69
0
4.51
24.
525
4.54
54.
558
4.62
14.
645
4.65
44.
678
4.99
75.
008
5.01
95.
030
5.04
25.
134
5.13
95.
144
6.19
16.
194
6.20
66.
209
7.05
07.
055
7.06
67.
070
7.26
27.
317
7.33
57.
354
7.37
57.
396
7.41
47.
508
7.82
67.
846
8.13
28.
150
18.1
90
1.03
71.
028
1.08
41.
019
0.99
6
1.12
52.
273
1.02
61.
030
1.08
3
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
28.1
7228
.207
35.5
43
62.9
40
73.1
5776
.682
77.0
0077
.317
84.4
9984
.621
115.
396
115.
608
119.
199
122.
707
123.
225
125.
459
128.
921
135.
480
146.
610
149.
308
149.
734
167.
979
NO2
NH
OBoc
NBoc
3l
NO2
NH
OBoc
NBoc
3l
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-45
NO2
NH
OBoc
NBoc
rac-3l
NO2
NH
OBoc
NBoc
3l
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-46
10 9 8 7 6 5 4 3 2 1 0 ppm
1.57
31.
678
1.70
51.
770
1.80
01.
832
1.93
21.
961
3.16
23.
171
3.18
13.
190
3.20
03.
210
3.22
03.
859
3.86
93.
894
3.90
44.
109
4.12
74.
144
4.16
24.
952
4.95
64.
960
6.19
56.
210
7.08
67.
101
3.83
00.
999
1.33
69.
084
1.20
93.
077
1.04
5
0.98
4
1.00
21.
028
1.00
7
0.97
6
1.00
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
25.9
9528
.014
30.7
2430
.769
39.1
2942
.795
61.6
57
73.3
4376
.682
77.0
0077
.318
83.9
44
129.
179
146.
315
148.
927
168.
341
NO2
NH
OBoc3m
NO2
NH
OBoc3m
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-47
NO2
NH
OBocrac-3m
NO2
NH
OBoc3m
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-48
10 9 8 7 6 5 4 3 2 1 0 ppm
1.34
61.
359
1.37
71.
394
1.41
21.
543
1.65
21.
668
1.68
51.
701
1.71
91.
736
1.75
23.
330
3.34
93.
360
3.36
73.
372
3.37
83.
390
3.40
83.
933
3.95
13.
965
3.98
44.
063
4.07
64.
095
4.10
84.
737
4.74
24.
747
6.18
46.
187
6.20
06.
203
7.11
17.
115
7.12
77.
131
7.26
0
6.01
8
2.22
38.
598
1.08
8
1.00
0
1.02
81.
185
1.06
3
1.03
6
1.02
3
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
22.1
5522
.655
25.3
2127
.975
35.8
7939
.152
63.0
86
75.3
9976
.727
77.0
4677
.364
83.8
99
129.
071
145.
915
148.
990
168.
381
NO2
NH
OBoc
3n
NO2
NH
OBoc
3n
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-49
NO2
NH
OBoc
rac-3n
NO2
NH
OBoc
3n
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-50
NO2
NH
OBoc
ent-3n
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-51
10 9 8 7 6 5 4 3 2 1 0 ppm
1.05
31.
070
1.13
51.
152
1.56
91.
750
1.76
71.
785
1.80
51.
822
1.83
93.
101
3.11
13.
121
3.12
93.
139
3.15
03.
160
3.88
93.
899
3.92
33.
934
4.10
44.
121
4.13
84.
155
4.92
84.
932
6.20
06.
204
6.21
66.
219
7.08
97.
093
7.10
47.
109
7.26
1
3.00
02.
986
9.07
61.
029
0.98
8
0.99
01.
008
0.98
2
0.95
9
0.98
0
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
20.5
6320
.645
27.9
7229
.490
43.8
78
61.9
91
73.5
3376
.682
77.0
0077
.318
83.9
18
129.
239
146.
110
148.
887
168.
308
NO2
NH
OBoc
3o
NO2
NH
OBoc
3o
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-52
NO2
NH
OBoc
rac-3o
NO2
NH
OBoc
3o
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-53
10 9 8 7 6 5 4 3 2 1 0 ppm
1.60
42.
851
2.86
52.
898
2.91
33.
101
3.12
43.
149
3.17
24.
365
4.37
94.
392
4.40
44.
417
4.44
74.
476
4.50
24.
547
4.55
94.
577
4.58
84.
646
4.66
84.
683
4.69
74.
712
4.72
04.
735
4.74
14.
757
7.00
57.
025
7.04
57.
064
7.08
27.
172
7.19
07.
285
7.30
47.
324
9.10
4
1.06
91.
000
1.01
01.
039
1.02
52.
142
1.10
01.
029
1.21
31.
015
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
27.9
17
38.4
3339
.153
59.9
36
70.4
3675
.296
76.6
8277
.000
77.3
1884
.903
118.
218
124.
156
125.
162
129.
403
130.
214
149.
162
154.
644
170.
225
NO2
NH
OBoc
OH H
4
NO2
NH
OBoc
OH H
4
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Ray Choudhury & Mukherjee, SI-Part-B, Page S-54
NO2
NH
OBoc
OH H
rac-4
NO2
NH
OBoc
OH H
4
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012