Oxadiazinones as chiral auxiliaries:: diastereoselective aldol addition reactions of N3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones

被引：15

作者：

Hoover, TR ^{[1
]}

Hitchcock, SR ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Normal, IL 61790 USA

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2003.07.020

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric aldol reactions have been conducted with a series of N-3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine. These reactions afford the non-Evans syn-adducts in 43-97% yield and diastereoselectivities ranging from 62:38 to 99:1. Oxadiazinone substrates substituted with either the phenoxyacetyl or p-methoxyphenoxyacetyl groups gave the best results whereas the methoxyacetyl substituted oxadiazinone afforded diastereoselectivities that were modest. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：3233 / 3241

页数：9

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