Preparation of enantiomerically enriched bromohydrins from [N-(p-tolylsulfonyl)sulfoximino]oxiranes using in situ reduction of α-bromo aldehydes

被引：9

作者：

Bailey, PL

Briggs, AD

Jackson, RFW

Pietruszka, J

机构：

[1] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 20期

关键词：

D O I：

10.1039/a805839c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of enantiomerically pure [N-(p-tolylsulfonyl)sulfoximino]oxiranes 6 with MgBr2 in the presence of tetrabutylammonium borohydride gives enantiomerically enriched bromohydrins 3, together with small amounts of the primary alcohols 11. The bromohydrins 3 are isolated in good yields with enantiomeric excesses in the range 70% to 91%. This process establishes that alpha-bromo aldehydes have sufficient configurational stability to be viable synthetic intermediates.

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页码：3359 / 3363

页数：5

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