New synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives

被引：32

作者：

Ella-Menye, JR ^{[1
]}

Sharma, V ^{[1
]}

Wang, GJ ^{[1
]}

机构：

[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

关键词：

D O I：

10.1021/jo040224q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DIAGRAM Chiral 1,3-oxazinan-2-ones are useful intermediates in synthesizing pharmaceutical compounds and amino alcohols. In this paper, we report a new synthetic method to chiral 6-hydroxymethyl 1,3-oxazinan-2-ones and their analogues from carbohydrate derivatives. The synthesis was accomplished by the reaction of optically pure 3-hydroxy-gamma-buty-rolactone with a primary a-mine to give an amide, which was reduced and carbonylated to give the desired compound class.

引用

页码：463 / 469

页数：7

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