Table 2. Enantioselective Nazarov cyclization of 2 cooperatively catalyzed by ZnCl2 and (R)-1e: influence of N-protecting groups a .
| ||||
| Entry | R2 | Product | Yield b (%) | er c |
| 1 | Me (2a) | 3a | 98 | 91 : 9 |
| 2 | iPr (2b) | 3b | 98 | 90 : 10 |
| 3 | Allyl (2c) | 3c | 93 | 89 : 11 |
| 4 | Bn (2d) | 3d | 87 | 88 : 12 |
| 5 | Ph (2e) | 3e | 90 | 92 : 8 |
| 6 | An (2f) | 3f | 95 | 92 : 8 |
| 7 | 4-CF3C6H4 (2g) | 3g | 76 | 91 : 9 |
| 8 | 2-Np (2h) | 3h | 92 | 92 : 8 |
aReaction conditions: ZnCl2/(R)-1e/2 = 0.01 : 0.012 : 0.2 (mmol) in 3 mL DCE, 40 °C, 48 h.
bIsolated yield.
cDetermined by HPLC using a Chiralpak AD-3 or Chiralcel OD-3 column.