α,α-二取代硼烯醇盐在季碳中心的不对称合成中应用
Alpha,alpha-disubstituted boron enolates in the asymmetric synthesis of quaternary carbon centers.
作者信息
Burke E Diane, Gleason James L
机构信息
Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, Canada, H3A 2K6.
出版信息
Org Lett. 2004 Feb 5;6(3):405-7. doi: 10.1021/ol0364428.
PMID:14748604
Abstract
[reaction: see text] Reduction of alpha,alpha-disubstituted thioglycolate amides with lithium di-tert-butylbiphenylide affords alpha,alpha-disubstituted enolates with high Z/E selectivity. Transmetalation of the enolates with dicyclohexylboron bromide facilitates highly diastereoselective aldol reaction with aromatic and alpha,beta-unsaturated aldehydes.
摘要
[反应：见正文] 用二叔丁基联苯锂还原α,α-二取代硫代乙醇酸酰胺可得到具有高Z/E选择性的α,α-二取代烯醇盐。烯醇盐与二环己基溴化硼进行金属转移，促进了与芳香醛和α,β-不饱和醛的高度非对映选择性羟醛反应。
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