Table 1.
Final Optimization of the Asymmetric, Conjugate Addition of BBA.
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entry | concentration | temperature | equiv of BBA | yield (%) | enantiomeric ratio[a] |
1 | 0.1 M | rt | 2 | 87 | 91:9 |
2 | 0.25 M | rt | 2 | 82 | 94:6 |
3 | 0.5 M | rt | 2 | 90 | 93:7 |
4 | 0.5 M | rt | 1.5 | 80 | 92:8 |
5 | 0.5 M | rt | 1.2 | 67 | 92:8 |
6 | 0.5 M | 0 °C | 2 | 77 | 93:7 |
Enantiomeric excess determined by oxidation of 2a to 6 followed by SFC analysis of 6