Stereoselective synthesis of terminal 1,3-butadienes by the condensation reaction of aldehydes and ketones with .gamma.-trimethylsilyl-substituted allylboranes
作者:Kung K. Wang、Chin Liu、Yu Gui Gu、Friedrich N. Burnett、Prem D. Sattsangi
DOI:10.1021/jo00005a045
日期:1991.3
Allylboranes 7-12, readily prepared from allenylsilanes 1-6 by hydroboration with 9-borabicyclo[3.3.1]nonane, smoothly condense with aldehydes and ketones to afford, after basic or acidic workup to promote the Peterson olefination reaction, a variety of terminal 1,3-butadienes. The dienes derived from aldehydes have high isomeric purity except in the cases with allylborane 12. Apparently, high diastereoselectivity was obtained during the condensation step with 7-11 to form 14. In each case, by simply changing the workup conditions to induce syn or anti elimination of hydroxytrimethylsilane, either the Z or the E isomer of the diene was obtained.