Initial screening of CPAsa.
| |||||
|---|---|---|---|---|---|
| Entry | CPA | Time (h) | Yield of 3aab (%) | endo/exoc | eec (%) |
| 1 | (R)-4a | 12 | 95 | 81 : 19 | 71/88 |
| 2 | (R)-4b | 36 | 95 | 88 : 12 | 5/−12 |
| 3 | (R)-4c | 36 | 67 | 87 : 13 | 5/−3 |
| 4 | (R)-5 | 20 | 95 | 74 : 26 | 71/NDd |
| 5 | (S)-6 | 74 | 62 | 99 : 1 | 88/NDd |
| 6e | (S)-6 | 5 d | 91 | 99 : 1 | 92/NDd |
Unless otherwise noted, all reactions were carried out using 0.1 mmol of 1a, 0.12 mmol of 2a, and 0.010 mmol of CPA catalyst (10 mol%) in toluene (1 mL).
Isolated yield.
Diastereomeric and enantiomeric excess were determined by chiral stationary phase HPLC analysis.
ND: not determined.
MS 5A (50 mg) was used as an additive.