Table 1. Reaction Optimization Conditionsa.
| entry | deviation in conditions | yield (%) |
|---|---|---|
| 1 | standard conditions | 79 (63%) |
| 2 | 2 equiv Zn(0) | 21 |
| 3 | 2 equiv Mn(0) | 24 |
| 4 | 2 equiv TDAE | 43 |
| 5 | no reductant | <1 |
| 6 | diethylzinc bromide | <1 |
| 7 | phenethylzinc bromide | 58 |
| 8 | no additives | 49 |
| 9 | dioxanylzinc bromide | 56 |
| 10 | cyclopropylzinc bromide | 59 |
| 11 | tert-butylzinc bromide | 46 |
| 12 | 1-ethylpropylzinc bromide | 70 |
| 13 | DMF instead of NMP | 66 |
| 14 | DMSO instead of NMP | 70 |
| 15 | toluene instead of NMP | 25 |
| 16 | THF instead of NMP | 29 |
| 17 | MeCN instead of NMP | 0 |
0.1 mmol scale reactions in 0.5 mL of solvent.1H NMR yields using pyrene as an internal standard. The value in parentheses is the isolated yield [diastereomeric ratio (dr) = 1:1] from 0.5 mmol. The dr was determined by 1H NMR of the crude reaction mixture.
