Et3B- and Et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions

被引：86

作者：

Bertrand, MP ^{[1
]}

Coantic, S ^{[1
]}

Feray, L ^{[1
]}

Nouguier, R ^{[1
]}

Perfetti, P ^{[1
]}

机构：

[1] Univ Aix Marseille 3, Fac Sci St Jerome, Lab Chim Mol Organ, UMR 6517, F-13397 Marseille 20, France

来源：

TETRAHEDRON | 2000年 / 56卷 / 24期

关键词：

radical additions; glyoxylate imines; triethylborane diethylzinc;

D O I：

10.1016/S0040-4020(00)00327-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Stereoinduction in the addition of alkyl radicals to glyoxylic imines derived from various chiral amines has been investigated. New synthetic methodologies involving Et3B and Et2Zn as mediators have been compared. Dihydro-1,4-oxazin-2-one (2b) gave the highest d.e. but no chemoselectivity. Open chain analogues derived from beta-alkoxyamines led to good stereoinduction when the reaction was performed with Et2Zn which is a bidentate complexing reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3951 / 3961

页数：11

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