ENANTIOSELECTIVE PREPARATION OF ALKYL ALKYLSULFANYLMETHYL SULFOXIDES AND 4,5-DIHYDROISOXAZOLES FROM ALKANESULFINATES OF 1.2/5,6-DI-O-ISOPROPYLIDENE-D-GLUCOSE

被引：8

作者：

ARROYOGOMEZ, Y ^{[1
]}

LOPEZSASTRE, JA ^{[1
]}

RODRIGUEZAMO, JF ^{[1
]}

SANTOSGARCIA, M ^{[1
]}

SANZTEJEDOR, MA ^{[1
]}

机构：

[1] UNIV VALLADOLID,EST INGENIEROS IND,DEPT QUIM ORGAN,E-47071 VALLADOLID,SPAIN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 15期

关键词：

D O I：

10.1039/p19940002177

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of (R) and (S)-alkanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucose (DAG) with methylsulfanylmethyllithium produces their corresponding dithioacetal mono-S-oxides with enantiomeric excesses ranging from 95 to 100%. On the other hand, exo-metallation of 3-methyl-4,5-dihydroisoxazoles and their subsequent reaction with (R)- and (S)-alkanesulfinates of DAG produces optically active 3-ethylsulfinylmethyl-4,5-dihydroisoxazoles.

引用

页码：2177 / 2180

页数：4

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