(+)-(S)-ALPHA-DIETHOXYPHOSPHORYLVINYL P-TOLYL SULFOXIDE - A NEW CHIRAL MICHAEL ACCEPTOR AND DIENOPHILE

被引：27

作者：

MIKOLAJCZYK, M

MIDURA, WH

机构：

[1] Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Organic Sulfur Compounds, Sienkiewicza 112

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)86048-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The title reagent, (+)-(S)-1, was prepared from (+)-(S)s-alpha-diethoxyphosphorylethyl p-tolyl sulfoxide 2 by phenylselenylation-deselenylation procedure. Its reactivity was demonstrated by diastereoselective Michael addition of ethanethiol giving rise to 3, tandem Michael addition/intramolecular Horner--Wittig reaction with 2-formyl pyrrole leading to the corresponding pyrrolizine sulfoxide 5 and cycloaddition with cyclopentadiene affording the diastereomeric adducts 6. The steric course of the Diels-Alder reaction is briefly discussed.

引用

页码：1515 / 1518

页数：4

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