Table 1 Asymmetric [3+2] coupling of 3-substituted indoles with quinone monoiminea
Entry | Cat. | R1 | R2 | R3 | Yield (%)b | ee (%)c |
---|---|---|---|---|---|---|
1 | 1-Ni | Me | H | H | 92 | 99.9 (S) |
2 | Me | Me | H | 90 | 95 (S) | |
3 | Me | H | 5-Me | 92 | 94 (S) | |
4 | Me | H | 6-F | 90 | 95 (S) | |
5 | Me | H | 6-Me | 95 | 99.9 (S) | |
6 | Me | H | 5-OMe | 86 | 91 (S) | |
7 | Me | H | 5-Br | 83 | 92 (S) | |
8d | Phenyl | H | H | 65 | 99.7 (S) | |
9d | Benzyl | H | H | 37 | 94 (S) | |
10d | PIMEe | H | H | 9 | n.d. | |
11 | Me | H | H | 94 | 99.9 (R)f | |
12 | 1-Co | Me | Me | H | 92 | 94 (S) |
13 | Me | H | 5-Me | 89 | 93 (S) | |
14 | Me | H | 6-F | 88 | 93 (S) | |
15 | PhCO2Hg | Me | H | H | n.d. | n.d. |
16 | 1-Ni*/Me4Lh | Me | H | H | 94 (79) | 89 (78) (S) |
17 | Me | H | 5-Me | 90 (77) | 87 (78) (S) | |
18 | Me | H | 6-F | 93 (76) | 89 (75) (S) | |
19 | Me | H | 5-Br | 91 (72) | 87 (76) (S) | |
20 | Phenyl | H | H | 70 (73) | 91 (80) (S) | |
21 | Benzyl | H | H | 69 (72) | 90 (87) (S) | |
22 | PIMEe | H | H | 56 (64) | n.d. (n.d.) |