Diastereoselective Strecker reaction of D-glyceraldehyde derivatives. A novel route to (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid.

被引：33

作者：

Cativiela, C

DiazdeVillegas, MD

Galvez, JA

Garcia, JI

机构：

[1] Inst. de Cie. de Mat. de Aragon, Depto. de Quimica Orgánica, Universidad de Zaragoza-C.S.I.C.

来源：

TETRAHEDRON | 1996年 / 52卷 / 28期

关键词：

D O I：

10.1016/0040-4020(96)00493-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient and stereoselective synthetic routes to enantiomerically pure (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid have been developed using the stereoselective Strecker type reaction of carbonyl compounds derived from appropriately protected D-glyceraldehyde. The stereoselectivity of the cyanide addition was shown to be dependent on the presence of metal complexing agents, which is essential in the case of (2R)-2,3-di-O-benzyl-D-glyceraldehyde. In addition, theoretical calculations to rationalize the stereochemical course of the reaction have been performed. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9563 / 9574

页数：12

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