A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides

被引：26

作者：

Andersen, NG ^{[1
]}

Ramsden, PD ^{[1
]}

Che, DQ ^{[1
]}

Parvez, M ^{[1
]}

Keay, BA ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 22期

关键词：

D O I：

10.1021/jo015909u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The resolution of a variety of (+/-)-P-stereogenic phosphines is achieved by exploiting the Staudinger reaction of a (+/-)-phosphine with enantiopure (1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonyl azide. The resulting mixtures of diastereomeric phosphinimines are generally separable by fractional crystallization or flash chromatography. Subsequent acid-catalyzed hydrolysis provides the corresponding optically pure phosphine oxides in high yields.

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页码：7478 / 7486

页数：9

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