Highly syn-diastereoselective Michael addition of enolizable ketones to 3-(diethoxyphosphoryl)coumarin

被引：12

作者：

Deredas, Dariusz ^{[1
]}

Huben, Krzysztof ^{[1
]}

Maniukiewicz, Waldemar ^{[2
]}

Krawczyk, Henryk ^{[1
]}

机构：

[1] Tech Univ Lodz, Inst Organ Chem, PL-90924 Lodz, Poland

[2] Tech Univ Lodz, Inst Gen & Ecol Chem, PL-90924 Lodz, Poland

来源：

TETRAHEDRON | 2014年 / 70卷 / 46期

关键词：

Michael addition; HWE olefination; Diastereoselectivity; 1,5,7-Triazabicyclo[4.4.0]dec-5-ene; Cesium carbonate; ALPHA; BETA-UNSATURATED ESTERS; CONDENSATION; ENOLATE; ROUTE;

D O I：

10.1016/j.tet.2014.09.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to 3-(diethoxyphosphoryl)-4-(2-oxoalkyl)-3,4-dihydrocoumarins by base promoted conjugate addition of enolizable ketones to 3-(diethoxyphosphoryl)coumarin is described. The resulting products were transformed into the corresponding alpha-methylene-delta-lactones. A transition state model rationalizing stereochemical outcome of the reaction is proposed. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：8925 / 8929

页数：5

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