Table 2. Substrate scope of enantioselective intramolecular SN2′ reaction a .
| ||||
| Entry | 1 and 2(R) | Conditions | Yield b (%) | ee c (%) |
| 1 d | b: 4-MeOC6H4– | –60 °C, 12 h | 98 | 79 |
| 2 d | c: 4-MeC6H4– | –60 °C, 12 h | 96 | 90 |
| 3 | d: 4-ClC6H4– | –50 °C, 48 h | 90 | 91 |
| 4 | e: 3-MeOC6H4– | –50 °C, 12 h | 90 | 90 |
| 5 | f: 3-MeC6H4– | –60 °C, 48 h | 97 | 91 |
| 6 | g: 3-ClC6H4– | –40 °C, 36 h | 88 | 88 |
| 7 | h: 3-CF3C6H4– | –40 °C, 48 h | 86 | 89 |
| 8 | i: 2-MeOC6H4– | –40 °C, 12 h | 90 | 60 |
| 9 | j: 2-MeC6H4– | rt, 24 h | Trace | — |
| 10 | k: 2-FC6H4– | –20 °C, 12 h | 87 | 87 |
| 11 d | l: 2-Naphthyl | –60 °C, 12 h | 85 | 86 |
| 12 | m: Ph–C C– | –40 °C, 48 h | 55 | 60 |
| 13 d | n: Thiophen-3-yl | –60 °C, 8 h | 95 | 91 |
aUnless otherwise noted, all reactions were carried out using 0.01 mmol of (R)-3d (10 mol%), 0.1 mmol of (E)-1, and MS 4A (50 mg) in chloroform (1.0 mL).
bIsolated yield.
cee was determined by chiral stationary phase HPLC analysis.
d5 mol% of (R)-3d was used.