Synthesis of β-heteroaryl propionates via trapping of carbocations with π-nucleophiles

被引：56

作者：

Fu, Tsung-hao ^{[1
]}

Bonaparte, Amy ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

基金：

美国国家卫生研究院;

关键词：

FRIEDEL-CRAFTS ALKYLATION; ELECTRON-DEFICIENT OLEFINS; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED KETONES; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; BRONSTED ACID; AMINO-ACIDS; INDOLES; ALCOHOLS;

D O I：

10.1016/j.tetlet.2009.02.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of heterocyclic alcohols and acetates were Coupled with silyl ketene acetals and other pi-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array Of Substituted beta-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the pi-nucleophile bears a chiral auxiliary. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3253 / 3257

页数：5

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