Ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes:: an expeditious diastereoselective approach for the preparation of α,β-dihydroxy-esters

被引：11

作者：

Abella, Carlos A. M. ^{[1
]}

Rezende, Patricia ^{[1
]}

de Souza, Michele F. Lino ^{[1
]}

Coelho, Fernando ^{[1
]}

机构：

[1] Unicamp IQ DQO, Lab Synth Nat Prod & Drug, BR-13084971 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 01期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/j.tetlet.2007.10.149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We disclose herein ozonolysis of Morita-Baylis-Hillman adducts originated from aromatic aldehydes. This efficient reaction provides alpha-ketoesters with different substitution patterns on the aromatic ring. Diastercoselective reduction of the corresponding alpha-ketoester obtained in the oxidative cleavage step provides alpha,beta-dihydroxy-esters with excellent degree of anti diastereoselection. The method is simple and easy to execute and is therefore a valuable alternative to prepare either alpha-ketoesters or alpha-dihydroxy-esters. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：145 / 148

页数：4

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