Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrolidine-2-carboxamides as new chiral auxiliaries for the asymmetric synthesis of (S)-α-amino acids

被引：18
作者：
Belokon, YN
Maleev, VI
Petrosyan, AA
Savel'eva, TF
Ikonnikov, NS
Peregudov, AS
Khrustalev, VN
Saghiyan, AS
机构：
[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
[2] Minist Ind Republ Armenia, Biotechnol Res Inst, Yerevan 375056, Armenia
来源：
RUSSIAN CHEMICAL BULLETIN | 2002年 / 51卷 / 08期
基金：
俄罗斯基础研究基金会;
关键词：
asymmetric synthesis; amino acids; chiral auxiliaries; nickel(II) complexes;
D O I：
10.1023/A:1020952115556
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of new chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide (1a), (,S)-N-(2-benzoylphenyl)-1-(pentafluorobenzyl)pyrrolidine2-carboxamide (1b), and (S)-N-(2-benzoylphenyl)-1-(4-isopropoxytetrafluorobenzyl)pyrrolidine-2-carboxamide (1c) and their application in the asymmetric synthesis of amino acids using Ni-II complexes of their Schiff's bases with alanine and glycine are described. Compound la is particularly appropriate for highly stereoselective synthesis of a-methyl-a-amino acids with high enatiomeric purity (ee >95%).
引用
收藏
页码：1593 / 1599
页数：7
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