Rapid, One-Pot Synthesis of β-Siloxy-α-haloaldehydes

被引：59

作者：

Saadi, Jakub ^{[1
]}

Akakura, Matsujiro ^{[2
]}

Yamamoto, Hisashi ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

[2] Aichi Univ Educ, Dept Chem, Kariya, Aichi 4488542, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 36期

关键词：

HETEROATOM-SUBSTITUTED ALDEHYDES; SUPER SILYL GROUP; BRONSTED ACID CATALYST; ALDOL CASCADE REACTION; MEDICINAL CHEMISTRY; STEREOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE ALDOL; ASYMMETRIC INDUCTION; SEQUENTIAL REACTIONS; ENOL ETHERS;

D O I：

10.1021/ja2066169

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Mukaiyama cross-aldol reaction of alpha-fluoro-, alpha-chloro-, and alpha-bromoacetaldehyde-derived (Z)tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-beta-siloxy-alpha-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel beta,delta-bissiloxy-alpha,gamma-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.

引用

页码：14248 / 14251

页数：4

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