Highly diastereoselective Michael reaction of (S)-mandelic acid enolate.: Chiral benzoyl carbanion equivalent through an oxidative decarboxylation of α-hydroxyacids

被引：18

作者：

Blay, G ^{[1
]}

Fernández, I ^{[1
]}

Monje, B ^{[1
]}

Pedro, JR ^{[1
]}

Ruiz, R ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(02)02099-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the lithium enolate of the 1,3-dioxolan-4-one derived front optically active (S)-mandelic acid and pivalaldehyde with alpha,beta-unsaturated carbonyl compounds proceeds readily to give the corresponding Michael adducts in good yields and high diastereoselectivity. Subsequent basic hydrolysis of the acetal and oxidative decarboxylation of the a-hydroxyacid moiety provides chiral 2-substituted 1,4-dicarbonyl compounds with very high enantionieric excesses. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8463 / 8466

页数：4

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