Table 3.
Conjugate Addition of Acetone Cyanohydrin to 7.a
| ||||||
|---|---|---|---|---|---|---|
| Entry | 7 | R | PTC | Time (h) | Yieldb | eec |
| 1d | 7a | Et | CPD-2 | 24 | >95e | 86 |
| 2d | 7a | Et | CPN-3 | 24 | >95e | 78 |
|
| ||||||
| 3 | 7a | Et | CPD-2 | 48 | 83 | 95 (S) |
| 4 | 7a | Et | CPN-3 | 24 | 94 | 90 (R) |
|
| ||||||
| 5 | 7b | Me | CPD-2 | 48 | 79 | 97 (S) |
| 6 | 7b | Me | CPN-3 | 24 | 77 | 92 (R) |
|
| ||||||
| 7 | 7c | n-C5H11 | CPD-2 | 96 | 87 | 96 (S) |
| 8 | 7c | n-C5H11 | CPN-3 | 24 | 84 | 92 (R) |
|
| ||||||
| 9 | 7d | iPr | CPD-2 | 48 | 83 | 95 (S) |
| 10 | 7d | iPr | CPN-3 | 24 | 71 | 91 (R) |
|
| ||||||
| 11 | 7e | CH2iPr | CPD-2 | 96 | 78 | 98 (S) |
| 12 | 7e | CH2iPr | CPN-3 | 24 | 80 | 94 (R) |
|
| ||||||
| 13 | 7f | CH2CH2Ph | CPD-2 | 96 | 75 | 95 (S) |
| 14 | 7f | CH2CH2Ph | CPN-3 | 24 | 70 | 93 (R) |
Unless noted reactions were performed with 0.1 mmol of 7 and 0.2 mmol acetone cyanohydrin, 0.12 mmol Rb2CO3 in 1 mL of Toluene/CHCl3 (7:3 v/v) with 10 mol% CPD-2(or 10 mol% CPN-3a).
Isolated yield.
Determined by chiral HPLC. The Absolute configuration is reported in parenthesis, see supporting information for details.
0.12 mmol Cs2CO3 used instead of Rb2CO3