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
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.
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页码:1667 / 1676
页数:10
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