Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines

被引：49

作者：

Blanchet, J ^{[1
]}

Bonin, M ^{[1
]}

Micouin, L ^{[1
]}

Husson, HP ^{[1
]}

机构：

[1] Univ Paris 05, UMR 8638 CNRS, Chim Therapeut Lab, Fac Sci Pharmaceut & Biol 4, F-75270 Paris 06, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 20期

关键词：

D O I：

10.1021/jo0003706

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 degrees C with dialkyl-alkynylalane-triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary alpha-substituted propargylamines cah be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.

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页码：6423 / 6426

页数：4

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