Diastereoselective construction of a new class of nicotine analogues having contiguous stereocenters via 1,3- dipolar cycloaddition
of azomethine ylides
Vadla Rajkumar & Srinivasarao Arulananda Babu*
Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli PO, Punjab, 140306, India
Email: sababu@iisermohali.ac.in
No. Contents Pg No.
1 NMR data of 4a 2
2 NMR data of 5a 6
3 NMR data of 4b 10
4 NMR data of 4c 14
5 NMR data of 5d 18
6 NMR data of 5e 22
7 NMR data of 5f 26
8 NMR data of 4g 30
9 NMR data of 4h/5h 34
10 NMR data of 4i 37
11 NMR data of 5i 41
12 NMR data of 6 44
13 NMR data of 7 48
14 NMR data of 8/9 52
15 NMR data of 11a 56
16 NMR data of 12a 59
17 NMR data of 11b 62
18 NMR data of 12b 66
18 NMR data of 13 69
20 NMR data of 14 73
21 NMR data of 15 77
22 NMR data of 17/18 80
23 NMR data of 22 83
24 NMR data of 24 87
25 NMR data of 25 91
26 NMR data of 26/27 95
27 NMR data of 29 100
28 NMR data of 30 104
29 NMR data of 31 107
N
N M
N O H 4a
2
N
N M
N O H 4a
3
N
N M
N O H 4a
4
N
N M
N O H 4a
5
N
N M
N O H 5a
6
N
N M
N O H 5a
7
N
N M
N O H 5a
8
N
N M
N O H 5a
9
N
N M
N O H 4b
10
N
N M
N O H 4b
11
N
N M
N O H 4b
12
N
N M
N O H 4b
13
N
N M
N O H
H3CO 4c
14
N
N M
N O H
H3CO 4c
15
N
N M
N O H
H3CO 4c
16
N
N M
N O H
H3CO 4c
17
5d
N
N M
N O H
Cl
18
5d
N
N M
N O H
Cl
19
5d
N
N M
N O H
Cl
20
5d
N
N M
N O H
Cl
21
5eN
N M
N O H
Cl
22
5eN
N M
N O H
Cl
23
5eN
N M
N O H
Cl
24
5eN
N M
N O H
Cl
25
N
N M
N O H
Br 5f
26
N
N M
N O H
Br 5f
27
N
N M
N O H
Br 5f
28
N
N M
N O H
Br 5f
29
N
N M
N O H 4g
30
N
N M
N O H 4g
31
N
N M
N O H 4g
32
N
N M
N O H 4g
33
N
N M
N O H 4i
37
N
N M
N O H 4i
38
N
N M
N O H 4i
39
N
N M
N O H 4i
40
5iN
N M
N O H
41
5iN
N M
N O H
42
5iN
N M
N O H
43
N
N M
N O
Ph H 6
44
N
N M
N O
Ph H 6
45
N
N M
N O
Ph H 6
46
N
N M
N O
Ph H 6
47
N
N M
N O
Ph H 7
48
N
N M
N O
Ph H 7
49
N
N M
N O
Ph H 7
50
N
N M
N O
Ph H 7
51
N
N Me
H EtOOC COO H 11a
56
N
N Me
H EtOOC COO H 11a
57
N
N Me
H EtOOC COO H 11a
58
N
N Me
H MeOOC COO H 11b
62
N
N Me
H MeOOC COO H 11b
63
N
N Me
H MeOOC COO H 11b
64
N
N Me
H MeOOC COO H 11b
65
12bN
N Me
H MeOOC COO H
66
12bN
N Me
H MeOOC COO H
67
12bN
N Me
H MeOOC COO H
68
N
N Me
H EtOOC COO H 14
73
N
N Me
H EtOOC COO H 14
74
N
N Me
H EtOOC COO H 14
75
N
N Me
H EtOOC COO H 14
76
N
N Me
H MeOOC COO H 17&18
80
N
N Me
H MeOOC COO H 17&18
81
N
N Me
H MeOOC COO H 17&18
82
N
NN O
Ph H Ph 22
83
N
NN O
Ph H Ph 22
84
N
NN O
Ph H Ph 22
85
N
NN O
Ph H Ph 22
86
N
NH MeOOCCOO H Ph 24
87
N
NH MeOOCCOO H Ph 24
88
N
NH MeOOCCOO H Ph 24
89
N
NH MeOOCCOO H Ph 24
90
N
NH MeOOC COO H Ph 25
91
N
NH MeOOC COO H Ph 25
92
N
NH MeOOC COO H Ph 25
93
N
NH MeOOC COO H Ph 25
94
N
NH EtOOC COO H Ph 26&27
95
N
NH EtOOC COO H Ph 26&27
96
N
NH EtOOC COO H Ph 26&27
97
N
NH EtOOC COO H Ph 26&27
98
N
NH EtOOC COO H Ph 26&27
99
