Stereocontrolled asymmetric synthesis of α-hydroxy-β-amino acids.: A stereodivergent approach

被引：40

作者：

Aoyagi, Y ^{[1
]}

Jain, RP ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2001年 / 123卷 / 15期

关键词：

D O I：

10.1021/ja0042332

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereocontrolled asymmetric synthesis of alpha -hydroxy-beta -amino acids has been investigated via the Lewis acid-promoted cyanation of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazines with trimethylsilyl cyanide. Base-catalyzed hydrolysis of the resulting cyano compounds proceeds with excellent stereoselectivity, providing access to diastereomerically pure oxazine-2-carboxylic acids which were readily converted to each enantiomer of the alpha -hydroxy-beta -amino acids isothreonine and nor-C-statine.

引用

页码：3472 / 3477

页数：6

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