DIASTEREOSELECTIVE REDUCTION OF CHIRAL N-TOSYL-2-BENZOYL-1,3-OXAZINE DERIVED FROM (1R)-(+)-CAMPHOR

被引：2

作者：

Ko, Kwang-Youn ^{[1
]}

Yun, Hoseop ^{[2
]}

机构：

[1] Ajou Univ, Dept Chem, Suwon 443749, South Korea

[2] Ajou Univ, Div Energy Syst Res, Suwon 443749, South Korea

来源：

HETEROCYCLES | 2010年 / 81卷 / 10期

关键词：

Reduction; Diastereoselectivity; 1,3-Oxazine; Chelate Model; (+)-Camphor; GLYCOLS RCHOHCH2OH; D-GLUCOSE; ADDITIONS; AUXILIARY; PURITY;

D O I：

10.3987/COM-10-12016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine prepared by condensation of 1,3-amino alcohol derived from (1R)-(+)-camphor with phenylglyoxal was investigated using various reducing agents. Based on X-ray crystallography, 2-benzoyl group in 1,3-oxazine ring was situated in the axial position. High diastereoselectivity observed in the hydride reduction can be explained by a chelate model where N-tosyl oxygen atom takes part in chelation rather than ring oxygen atom.

引用

页码：2351 / 2359

页数：9

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