Stereodivergent approach to β-hydroxy α-amino acids from C2-symmetrical alk-2-yne-1,4-diols

被引：29

作者：

Amador, M ^{[1
]}

Ariza, X ^{[1
]}

Garcia, J ^{[1
]}

Sevilla, S ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 25期

关键词：

D O I：

10.1021/ol0270428

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.

引用

页码：4511 / 4514

页数：4

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