PHENYLSULPHONYLOXIRANES AS FUNCTIONALIZED ACYL ANION EQUIVALENTS IN ORGANIC-SYNTHESIS

被引：63

作者：

ASHWELL, M ^{[1
]}

CLEGG, W ^{[1
]}

JACKSON, RFW ^{[1
]}

机构：

[1] UNIV NEWCASTLE UPON TYNE,DEPT CHEM,BEDSON BLDG,NEWCASTLE TYNE NE1 7RU,TYNE & WEAR,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 04期

关键词：

D O I：

10.1039/p19910000897

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenylsulphonyloxiranes can be lithiated with butyllithium alpha to the phenylsulphonyl group at low temperature. The anions formed are unstable, but sufficiently reactive to allow the isolation of adducts in good yield following treatment with a variety of electrophiles. Reaction of functionalised phenylsulphonyloxiranes with magnesium bromide-diethyl ether at room temperature allows the preparation of synthetically useful alpha-bromo ketones with complete regiocontrol.

引用

页码：897 / 908

页数：12

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