Diastereoselective aldol condensation of acylsilane silyl enol ethers with acetals

被引：26

作者：

Honda, M ^{[1
]}

Oguchi, W ^{[1
]}

Segi, M ^{[1
]}

Nakajima, T ^{[1
]}

机构：

[1] Kanazawa Univ, Fac Engn, Dept Chem & Chem Engn, Kanazawa, Ishikawa 9208667, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 34期

关键词：

acetals; aldol reactions; diastereoselection; enol ethers; silicon and compounds;

D O I：

10.1016/S0040-4020(02)00787-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of E- or Z-acylsilane silyl enol ethers derived from acylsilanes having an enolizable methylene proton with a mixture of aromatic aldehyde dimethyl acetals and TiCl4 in dichloromethane gives the corresponding 2,3-anti-3-methoxyacylsilanes in high d.e., independent of the geometry of double bond in acylsilane silyl enol ethers. On the other hand, E-acylsilane silyl enol ethers react with acetals of aliphatic aldehydes to afford the corresponding aldol adducts with syn-selectivity, while the reaction of Z-isomers provides the products with anti-selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6815 / 6823

页数：9

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