Diastereoselective Synthesis of γ-Amino Acids and Their Derivatives from Nitroethane via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines Bearing the CH2CH(CO2Me)2 Substituent at C3

被引：17

作者：

Sukhorukov, Alexey Yu. ^{[1
]}

Lesiv, Alexey V. ^{[1
]}

Khomutova, Yulia A. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2009年 / 05期

基金：

俄罗斯基础研究基金会;

关键词：

5,6-dihydro-4H-1,2-oxazines; reduction; gamma-amino acids; oxyiminium cations; CONVENIENT PROCEDURE; 6-SILOXY-SUBSTITUTED 5,6-DIHYDRO-4H-1,2-OXAZINES; PYRROLE DERIVATIVES; REDUCTION; HYDROGENATION; DEOXYGENATION; REACTIVITY; ALPHA;

D O I：

10.1055/s-0028-1083360

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective two-step reduction of available 2-[(5,6-dihydro-4H-1,2-oxazin-3-yl)methyl]malonates provides an efficient route to derivatives of different gamma-amino acids. The mechanism and stereochemistry of the first step, reduction of the C=N bond with sodium cyanoborohydride, is discussed.

引用

页码：741 / 754

页数：14

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