Table 4.
entry | imine | unsaturated alkoxide |
yield[a] [%] |
major regioisomer |
---|---|---|---|---|
1 | 65 | |||
2 | 100 | 103;R=Et | 60 | 104;R=Et |
3 | 100 | 105;R=iPr | 53 | 106;R=iPr |
4 | 100 | 107; R = TMS | 55 | 108; R = TMS |
Reaction conditions: Ti(OiPr)4, cC5H9MgCl, Et2O, −78 to −40 °C, then add unsaturated alkoxide (−40 to 0 °C), quench with sat. NH4Cl(aq).