Table 1. Condition Optimizationa.
| Entry | Reaction partners | L | X | Conv of 1a (%) | Yield (%) of 3 (α:β) |
|---|---|---|---|---|---|
| 1 | α-1a and 2a | L1 | NTf2 | 99 | 89 (1:14.8) |
| 2 | L2 | NTf2 | 99 | 87 (1:19.3) | |
| 3 | L2 | OTf | 99 | 98 (1:1.6) | |
| 4 | L3 | NTf2 | 99 | 95 (1:10.2) | |
| 5 | L4 | NTf2 | 99 | 86 (1:12.8) | |
| 6 | L5 | NTf2 | 99 | 91 (1:13.2) | |
| 7 | L6 | NTf2 | 99 | 91 (1:11.7) | |
| 8 | L7 | NTf2 | 99 | 99 (1:9.9) | |
| 9 | PPh3 | NTf2 | 99 | 94 (1:6.3) | |
| 10 | β-1a and 2a | L2 | NTf2 | 99 | 94 (4.2:1) |
| 11 | β-1a and 2b | L2 | NTf2 | 99 | 97 (7.4:1) |
| 12 | L2 | OMs | <5 | N. D. | |
| 13 | L2 | OTs | <5 | N. D. | |
| 14 | L2 | BF4 | 38 | 35 (>20:1) | |
| 15 | L2 | PF6 | 99 | 84 (13.1:1) | |
| 16 | L2 | OTf | 99 | 98 (15.4:1) | |
| 17 | PPh3 | OTf | 99 | 96 (1:2.2) | |
| 18 | L8 | OTf | 99 | 98 (1:1.8) | |
| 19 | L2 | BArF4 | 99 | 99 (1.7:1) | |
| 20 | PPh3 | BArF4 | 86 | 82 (1.8:1) |
Reactions were carried out at 0.05 mmol scale. Yields and conversions (conv) were determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard. The ratios of 3a epimers were collected by the 1H NMR analysis of the crude reaction mixture. N. D. = not determined. Ad = 1-adamantyl. BArF4 = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate.
