Table 1. Reaction optimization. Full optimization data available in the ESI.
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Entry | Catalyst | Solvent | Yield a (%) | er b |
1 (ref. 14) | A | THF | 12 | 53 : 47 |
2 | B | THF | 80 | 83 : 17 |
3 c | C | THF | 92 | 86 : 14 |
4 | D | THF | 83 | 66 : 34 |
5 | E | THF | 95 | 83 : 17 |
6 | F | THF | 90 | 90 : 10 |
7 d | None | THF | 95 | 50 : 50 |
8 e | F | Et2O | 93 | 94 : 6 |
9 f | F | Et2O | 88 | 82 : 18 |
10 e | G | Et 2 O | 98 | 95 : 5 |
aIsolated yield.
bDetermined by HPLC analysis on a chiral stationary phase.
cReaction carried out at 0.25 M concentration.
dReaction carried out over 72 h.
eReaction carried out at 0 °C, using 1.2 eq. of thiol and 0.06 M concentration.
fReaction carried out at –40 °C, using 1.2 eq. of thiol and 0.06 M concentration.