Asymmetric syntheses of new functionalized β-amino alcohols via diastereoselective addition of organometallic reagents onto oxazolidines

被引：32

作者：

Agami, C ^{[1
]}

Comesse, S ^{[1
]}

Kadouri-Puchot, C ^{[1
]}

机构：

[1] Univ Paris 06, UMR CNRS 7611, Lab Synth Asymetr, F-75005 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 05期

关键词：

D O I：

10.1021/jo010779a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective reactions between (S)-phenylglycinol-derived oxazolidines and two unsaturated organolithium reagents afforded chiral beta-amino alcohols having vinyl and alkynylsilane moieties. When the same reactions were performed in the presence of titanium isopropoxide, a dramatic change of regioselectivity was observed, from the alpha- to the gamma-position, thus producing beta-amino alcohols with allyl or allenylsilane functions. A rationalization of the observed diastereoselectivity was suggested for each case.

引用

页码：1496 / 1500

页数：5

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