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Optimization of the neopentyl 1,2-addition.
| |||
|---|---|---|---|
| entry | Li-I exchange | 1,2-addition | yield |
| 1 a | −78 °C, 60 min | −78 °C, 60 min | 5% 79, 30% 80 |
| 2 a | −78 °C, 10 min 0°C, 10 min | −78 °C to 0 °C , 60 min | 42% |
| 3 a | −78 °C, 10 min 0°C, 10 min | 0 °C, 60 min | 57% |
| 4 b | −78 °C, 10 min 25 °C, 15 min | 25 °C, 60 min | 83%, 200 mg scale |
| 5 b | −78 °C, 10 min 25 °C, 15 min | 25 °C, 60 min | 66%, 500 mg scale |
| 6 b | entry 4, quenched with 1 equiv. TMSCI | 25% 81 | |
| a: 1.0 equiv. 66 was used. b: 1.2 equiv. 66 was used. | |||
| |||
