AN EASY SYNTHESIS OF CHIRAL SULFINYL ALLYLIC BROMIDES AND THEIR USE IN THE PREPARATION OF (R)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES AND (S)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES

被引：29

作者：

BONFAND, E ^{[1
]}

GOSSELIN, P ^{[1
]}

MAIGNAN, C ^{[1
]}

机构：

[1] UNIV MAINE,CNRS,SYNTHESE ORGAN LAB,AVE OLIVIER MESSIAEN,BP 535,F-72017 LE MANS,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)80374-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Condensation of (R)-vinyl-p-tolylsulfoxide anion on carbonyl compounds led directly to chiral allylic sulfinylalcohols 1. By treatment with NBS/Me2S, these alcohols 1 were converted into the rearranged primary allylic bromides 2 via SN2' displacement. Optically pure (R)- and (S)-2-p-tolylsulfinyl-1,3-alkadienes 3 resulted from the action of KOH/ROH upon these bromides 2 via E2' eliminations.

引用

页码：1667 / 1676

页数：10

共 12 条

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