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路易斯酸的路易斯碱活化。非手性甲基酮的硅烯醇醚对醛的催化对映选择性加成。

Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes.

作者信息

Denmark Scott E, Heemstra John R

机构信息

Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, USA.

出版信息

Org Lett. 2003 Jun 26;5(13):2303-6. doi: 10.1021/ol034641l.

Abstract

A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield. [reaction: see text]

摘要

描述了一种从简单甲基酮衍生的硅烯醇醚的高度对映选择性加成反应。由手性双磷酰胺(R,R)-7活化的四氯化硅催化剂体系有效地促进了各种未取代的硅烯醇醚与芳族、烯烃和杂芳族醛的加成反应,产率优异。[反应:见正文]

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