Tandem Mukaiyama Michael-aldol reactions catalysed by samarium diiodide

被引：34

作者：

Giuseppone, N ^{[1
]}

Collin, J ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol Orsay, ESA 8075, Lab Catalyse Mol, F-91405 Orsay, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 43期

关键词：

samarium diiodide catalysis; tandem reactions; Michael reactions; aldol reactions;

D O I：

10.1016/S0040-4020(01)00902-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium diiodide is an efficient precatalyst for tandem Michael-aldol reactions, which allow the formation of two carbon-carbon bonds by successive additions of a ketene silyl acetal and an aldehyde on cyclic alpha,beta -unsaturated ketones. The adducts are isolated as silyl ethers, in good yields, and in some cases with high diastereoselectivities when the reactions are performed at low temperatures. Comparative study of the activities of other lanthanide iodides for the same tandem reactions is presented. A key step for a formal synthesis of PGF(2 alpha) has been performed by a tandem Michael-aldol samarium-catalysed sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8989 / 8998

页数：10

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