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.
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页码：741 / 754
页数：14
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