Asymmetric synthesis of polyhydroxy α-amino acids with the sulfinimine-mediated asymmetric strecker reaction:: 2-amino 2-deoxy L-xylono-1,5-lactone (Polyoxamic acid lactone)

被引：36

作者：

Davis, FA ^{[1
]}

Prasad, KR

Carroll, PJ

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 22期

关键词：

D O I：

10.1021/jo020302e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polyhydroxylated sulfinimines derived from protected 1,2-O-isopropyliden-L-threoses undergo the sulfinimine-mediated Strecker syntheses to give alpha-amino nitriles in good yield and de. A double stereodifferentiation effect was not observed and the diastereoselectivity is controlled by the absolute configuration of the sulfinyl group. Hydrolysis of the amino nitriles afforded the lactone rather than polyoxamic acid.

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页码：7802 / 7806

页数：5

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