Asymmetric synthesis of β-heterocycle substituted L-α-amino acids

被引：21
|
作者：
Saghiyan, AS
Geolchanyan, AV
Petrosyan, SG
Ghochikyan, TV
Haroutunyan, VS
Avetisyan, AA
Belokon, YN
Fisher, K
机构：
[1] Yerevan State Univ, Dept Chem, Yerevan 375049, Armenia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
[3] Univ Rostock, Inst Organ Catalysis IFOK, D-180055 Rostock, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期
关键词：
D O I：
10.1016/j.tetasy.2003.12.007
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A new efficient method of asymmetric synthesis of beta-heterocycle substituted L-alpha-amino acids through the addition of 3-amino-1,2,4-thiodiazole and 5-mercapto-1,2,4-triazoles, containing various substituents at the 3 and 4 positions, to the C=C bond of dehydroalanine in the Ni(II) complex of its Schiff base with (S)-2-N-(N-benzylprolyl) aminobenzophenone has been elaborated upon. Under thermodynamic control, the stereo selectivity of the nucleophilic addition exceeded 94%. After acidic decomposition of the reaction mixtures, the corresponding beta-heterocycle substituted alpha-amino acids with high enantiomeric purity (ee>98.5%) were isolated. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：705 / 711
页数：7
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