Table 2.
The scope of acceptorsa
| |||||||
|---|---|---|---|---|---|---|---|
| En-try | Sub-strate | Acceptor | Temp (°C) | Time (h) | 2 | Yieldb | α:βc |
| 1 | α-1b | isopropanol | −30 → −20 | 50 | 2b | 92% | 1:7.5 |
| 2 | β-1b | −40 | 48 | 2b | 91% | 9:1 | |
|
| |||||||
| 3 | α-1b |
|
−40 → −30 | 48 | 2c | 88% | 1:4 |
| 4 | β-1b | −40 → −30 | 36 | 2c | 87% | 23:1 | |
|
| |||||||
| 5 | α-1b | BnOH | −40 → −30 | 48 | 2d | 93% | 1:6.7 |
| 6 | β-1b | −40 | 48 | 2d | 95% | 10:1 | |
|
| |||||||
| 7 | α-1b | t-BuOH | −40 → −30 | 48 | 2e | 91% | 1:6.5 |
| 8 | β-1b | −30 | 36 | 2e | 92% | 6.7:1 | |
|
| |||||||
| 9 | α-1b |
|
−40 → −30 | 48 | 2f | 87% | 1:11 |
| 10 | β-1b | −30 | 36 | 2f | 89% | 10:1 | |
|
| |||||||
| 11 | α-1b | cholesterol | −20 | 36 | 2g | 85% | 1:8 |
| 12 | β-1b | −30 | 36 | 2g | 86% | 8:1 | |
|
| |||||||
| 13 | α-1b |
|
−20 | 36 | 2h | 60% | 1:2 |
| 14 | β-1b | −30 | 36 | 2h | 85% | 2.2:1 | |
|
| |||||||
| 15 | β-1b |
|
rt | 8 | 2i | 58% | 1.6:1 |
|
| |||||||
| 16 | β-1b |
|
0 | 8 | 2j | 83% | 2:1 |
Reactions were performed in sealed vials or Schlenk tube.
Isolate yields.
α:β ratio determined by crude 1H NMR.