1. Optimization of the Reaction Conditions .
| entry | 1 | (R)-3 | solvent | anti/syn, | ee (%) |
|---|---|---|---|---|---|
| 1 | 1a | (R)-3a | toluene | 60/40 | 96 |
| 2 | 1a | (R)-3a | CH2Cl2 | 64/36 | 95 |
| 3 | 1a | (R)-3a | THF | 85/15 | 95 |
| 4 | 1a | (R)-3a | Et2O | 94/6 | 97 |
| 5 | 1a | (R)-3b | Et2O | 95/5 | 98 |
| 6 | 1a | (R)-3c | Et2O | 91/9 | 98 |
| 7 | 1b | (R)-3a | Et2O | 84/16 | 95 |
| 8 | 1b | (R)-3b | Et2O | 83/17 | 88 |
Reaction conditions: 1 (0.20 mmol), 2a (0.30 mmol, 1.5 equiv), and (R)-3 (5 mol %, 0.01 mmol) in the indicated solvent (2 mL, 0.1 M) under a nitrogen atmosphere unless otherwise specified.
A diastereomeric mixture of 4 was obtained quantitatively in all cases.
The diastereomeric ratio was determined by 1H NMR measurements after short path silica-gel column chromatography.
The enantiomeric excess of the major anti-diastereoisomer was determined by HPLC analysis using a chiral stationary phase column.
A 93% ee for the syn-isomer.
A 60% ee for the syn-isomer.
