Nickel-Catalyzed Reductive Conjugate Addition to Enones Via Allylnickel Intermediates. Supporting Information NMR Spectra
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1 S51 Nickel-Catalyzed Reductive Conjugate Addition to Enones Via Allylnickel Intermediates Ruja Shrestha, Stephanie C. M. Dorn and Daniel J. Weix*. *Department of Chemistry, University of Rochester, Rochester, NY Present Address: Department of Chemistry, University of California, Berkeley, CA Supporting Information NMR Spectra VIII. NMR Spectra (separate pdf file) Compound 1 1 H NMR Compound 1 13 C NMR Compound 1 IR spectrum Compound 2 1 H NMR Compound 2 13 C NMR Compound 3 1 H NMR Compound 3 13 C NMR Compound 4 1 H NMR Compound 4 13 C NMR Compound 5 1 H NMR Compound 5 13 C NMR Compound 6 1 H NMR Compound 6 13 C NMR Compound 7 1 H NMR Compound 7 13 C NMR Compound 8 1 H NMR Compound 8 13 C NMR Compound 9 1 H NMR Compound 9 13 C NMR Compound 10 1 H NMR Compound C NMR Compound 11 1 H NMR Compound C NMR Compound 12 1 H NMR Compound C NMR Compound 13 1 H NMR Compound C NMR Compound F NMR Compound 14 1 H NMR Compound C NMR Compound 15 1 H NMR Compound C NMR Compound 16 1 H NMR Compound C NMR Compound 17 1 H NMR Compound C NMR Compound 18 1 H NMR Compound C NMR Compound 18 IR spectrum Compound 19 1 H NMR Compound C NMR Compound 20 1 H NMR Compound C NMR Compound 21 1 H NMR S53 S54 S55 S56 S57 S58 S59 S60 S61 S62 S63 S64 S65 S66 S67 S68 S69 S70 S71 S72 S73 S74 S75 S76 S77 S78 S79 S80 S81 S82 S83 S84 S85 S86 S87 S88 S89 S90 S91 S92 S93 S94 S95 S96
2 S52 Compound C NMR S97 Compound 22 1 H NMR S98 Compound C NMR S99 Compound 23 1 H NMR S100 Compound C NMR S101 Compound F NMR S102 Compound 24 1 H NMR S103 Compound C NMR S104 Compound 25 1 H NMR S105 Compound C NMR S106 Compound F NMR S107 Compound 26 1 H NMR S108 Compound C NMR S109 Compound F NMR S110 Compound 27 1 H NMR S111 Compound C NMR S112 Compound F NMR S113 Compound 28 1 H NMR S114 Compound C NMR S115 Compound 29 1 H NMR S116 Compound C NMR S117 Compound 30 1 H NMR S118 Compound C NMR S119 Compound 31 1 H NMR S120 Compound C NMR S121 Compound F NMR S122 Compound 32 1 H NMR S123 Compound C NMR S124 Compound 33 1 H NMR S125 Compound C NMR S126 Compound 34 1 H NMR S127 Compound C NMR S128
3 ppm Scheme 1 1 S53
4 S Scheme ppm
5 S55
6 ppm Me Scheme 1 2 S56
7 S Scheme 1 Me ppm
8 ppm Scheme 1 3 S58
9 S Scheme ppm
10 ppm O OMe 4 Scheme 1 S60
11 S OMe O 4 Scheme ppm
12 ppm O O 5 Scheme 1 S62
13 S O O 5 Scheme ppm
14 ppm O O 1 : 1 ratio of diastereomers 6 Scheme 1 S64
15 S O O 6 Scheme 1 1 : 1 ratio of diastereomers ppm
16 ppm O O 6 : 1 ratio of diastereomers Scheme 1 7 S66
17 S O O 7 Scheme 1 6 : 1 ratio of diastereomers peaks picked for major diastereomer only peaks for minor diastereomer could not be resolved ppm
18 ppm Scheme 1 8 OSi n Pr 3 Me S68
19 S OSi n Pr 3 8 Scheme 1 Me ppm
20 ppm OSiMe 2 t Bu Me 9 Scheme 1 S70
21 S OSiMe 2 t Bu 9 Scheme 1 Me ppm
22 ppm Me Scheme 2 10 S72
23 S Me 10 Scheme ppm
24 ppm OMe Scheme 2 11 S74
25 S OMe 11 Scheme ppm
26 ppm NMe 2 Scheme 2 12 S76
27 S Scheme 2 NMe ppm
28 ppm ppm F Scheme 2 13 S78
29 S Scheme 2 F ppm
30 S Scheme 2 F ppm
31 ppm O Me Scheme 2 14 S81
32 ppm S Me 14 Scheme 2 O
33 ppm CN Scheme 2 15 S83
34 ppm S Scheme 2 CN
35 ppm OMe 16 Scheme 3 S85
36 ppm S OMe 16 Scheme 3
37 ppm CN Scheme 3 17 S87
38 ppm S CN 17 Scheme 3
39 ppm Scheme 3 S89
40 ppm S Scheme 3
41 S91
42 ppm Cl Scheme 4 19 S92
43 ppm S Scheme 4 Cl
44 ppm Br Scheme 4 20 S94
45 ppm S Scheme 4 Br
46 ppm B O O Scheme B O O 21' major minor S96
47 ppm S O B O 21 Scheme 4
48 ppm SO 2 Me Scheme 4 22 S98
49 ppm S Scheme 4 SO 2 Me
50 ppm SF 5 23 Scheme 4 S100
51 ppm S Scheme 4 SF 5
52 ppm S Scheme 4 SF
53 ppm O H Scheme 4 24 S103
54 ppm S H 24 Scheme 4 O
55 ppm CF 3 Scheme 4 25 S105
56 ppm S Scheme 4 CF 3
57 ppm S Scheme 4 CF 3
58 ppm CF 3 26 Scheme 4 S108
59 ppm S CF 3 26 Scheme 4 hexane
60 ppm S CF 3 26 Scheme 4
61 ppm Me F Scheme 4 27 S111
62 ppm S F 27 Scheme 4 Me
63 ppm S F Me 27 Scheme 4
64 ppm CO 2 Me Scheme CO 2 Me 28' major minor S114
65 ppm S Scheme 4 CO 2 Me
66 ppm OEt O Scheme 4 29 S116
67 ppm S O OEt 29 Scheme 4
68 ppm O Me O Scheme 4 30 S118
69 ppm S O 30 Scheme 4 O Me
70 ppm Scheme 4 31 N H O CF 3 S120
71 ppm S O 31 Scheme 4 N H CF 3 Et 2 O Et 2 O
72 ppm S O 31 Scheme 4 N H CF 3
73 ppm O O Scheme O O 32' major minor S123
74 ppm S O 32 Scheme 4 O
75 ppm Scheme 4 33 S125
76 ppm S Scheme 4
77 ppm Me Scheme 4 34 S127
78 ppm S Me 34 Scheme 4
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