Initial results of the Michael reactiona.
| Entry | Catalyst | Time (h) | NMR yield of 3ab (%) | d.r.c | eed (%) |
|---|---|---|---|---|---|
| 1 | — | 48 | NR | ND | ND |
| 2 | A | 48 | 89 | 85 : 15 | −39/−40 |
| 3 | B | 22 | 84 | 87 : 13 | 40/43 |
| 4 | C e | 24 | 48 | 77 : 23 | 26/28 |
| 5 | B e | 24 | 86 | 85 : 15 | 45/46 |
Unless otherwise noted, all reactions were carried out with 0.1 mmol of 1a, 0.2 mmol of 2, and 0.02 mmol of catalyst in 0.2 mL of DCM at RT; NR – no reaction, ND – not determined.
Relative amount of 3a compared to the total amount of 1a, 3a and 5; determined from the reaction mixture by 1H NMR spectroscopy.
Determined from the reaction mixture by 1H NMR spectroscopy.
Determined by HPLC analysis on a chiral stationary phase.
10 mol% of catalyst instead of 20 mol% and (MeO)3C6H3 was used as an internal standard.