Table 2.
Substrate Scope of Trifluoromethyl Imines with Various Acrylatesa

| entry | R1; 1 | 4 | t (h) | yield of 5 (%)b | ee of 5 (%)c |
|---|---|---|---|---|---|
| 1d | Me; 1A | 4a | 8 | 80 (85); 5Aa | 92(92) |
| 2e | Me; 1A | 4b | 3 | 89 (92); 5Ab | 91 (93) |
| 3d | Me; 1A | 4c | 20 | 70 (75); 5Ac | 85 (90) |
| 4d | Me; 1A | 4d | 20 | 50 (63); 5Ad | 81 (86) |
| 5e | Me; 1A | 4e | 8 | 91 (93); 5Ae | 94 (94) |
| 6d | Et; 1B | 4a | 5 | 71 (73); 5Ba | 87 (90) |
| 7 | n-Bu; 1C | 4a | 8 | 63 (68); 5Ca | 91 (91) |
| 8 | CH2=CH(CH2)3; 1D | 4a | 8 | 64 (68); 5Da | 90 (92) |
| 9 | Ph(CH2)2; 1E | 4a | 8 | 53 (55); 5Ea | 90 (88) |
| 10f | H; 1F | 4a | 4 | 62 (70); 5Fa | 90 (91) |
| 11 | Cy; 1G | 4a | 8 | -- (--); 5Ga | -- (--) |
| 12 | Cy; 1G | 4b | 8 | 65 (63); 5Gb | 91 (93) |
| 13 | CyCH2; 1H | 4b | 8 | 71 (72); 5Hb | 90 (93) |
| 14 | Bn; 1I | 4b | 8 | 63 (72); 5Ib | 90 (92) |
| 15 | 4-BrBn; 1J | 4b | 8 | 68 (66); 5Jb | 88 (91) |
Unless noted, reactions were performed with 1 (0.2 mmol), acrylates 4 (0.4 mmol), A-1 (2.0 mol %), ethanol (20 μL) and aqueous KOH solution (2.2 μL, 50 wt %, 10 mol %) in PhMe (2.0 mL) with catalyst QD-3 (5.0 mol %) at the indicated temperature; results in parentheses were obtained from reactions catalyzed by epiQ-3 (5.0 mol %) in same conditions.
Isolated yield of 5.
Determined by HPLC analysis.
Reaction was performed at −40 °C.
1.0 mol % catalyst was used.
Reaction was performed at −50 °C