Table 2. Effect of Et3Na,b.
entry | catalyst (mol%) | additive (mol%) | yield (%) | ee (%) |
---|---|---|---|---|
1 | 2 (10) | none | 70 | 88 |
2 | 2·HCl (10) | none | 21 | 18 |
3 | 2·HCl (10) | Et3N (50) | 76 | 84 |
4 | 2 (10) | Et3N (50) | 95 | 99 |
5 | 2 (10) | Et3N (25) | 96 | 99 |
6 | 2 (5) | Et3N (25) | 83 | 94 |
7c | 2 (10) | Et3N (50) | 70 | 93 |
Conditions: substrate (0.05 mmol), catalyst (10 mol%), diketone (0.1 mmol), DCM (1 mL), under N2, initially cooled to −78 °C and stirred at −0 °C, 36 h.
The yield was determined by the 1H NMR analysis of the crude product using CH2Br2 as the internal standard.
Reaction carried out in the absence of added 4 Å MS.