CHIRAL ORTHOESTERS IN ORGANIC-SYNTHESIS - NOVEL REAGENTS FOR THE ENANTIOSELECTIVE ACYLATION OF SILYLENOLETHERS

被引：16

作者：

LONGOBARDO, L ^{[1
]}

MOBBILI, G ^{[1
]}

TAGLIAVINI, E ^{[1
]}

TROMBINI, C ^{[1
]}

UMANIRONCHI, A ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON | 1992年 / 48卷 / 07期

关键词：

CHIRAL ACYL CATIONS; ASYMMETRIC SYNTHESIS; ORTHOESTERS; ACYLATION; SILYLENOLETHERS;

D O I：

10.1016/S0040-4020(01)90792-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the presence of Lewis acids to give enantiomerically enriched (up to 90% d.e.) monoprotected 1,3-diketones. A dramatic dependence of the stereochemical outcome from the configuration of the enolic double bond of 4 has been observed. The products can be stereoselectively reduced to give configurationally defined monoprotected 3-ketols.

引用

页码：1299 / 1316

页数：18

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