Asymmetric synthesis of α-methyl α-amino acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure

被引：0
|
作者：
Nájera, C [1 ]
Abellán, T [1 ]
Sansano, JM [1 ]
机构：
[1] Univ Alicante, Fac Sci, Dept Organ Chem, E-03080 Alicante, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 15期
关键词：
amino acids; asymmetric synthesis; pyrazinones; phase-transfer catalysis; palladium;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(6R)-6-Isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone, obtained from (R)-valine and (S)-alanine, is highly diastereoselectively alkylated at room temperature by: a) activated alkyl halides under solid-liquid PTC conditions, b) non-activated alkyl halides with organic bases, c) electrophilic olefins employing both solid-liquid PTC conditions and organic bases, and d) allylic carbonates by means of palladium catalysis under neutral conditions. Enantiomerically pure (S)-alpha-methyl alpha-amino acids 8 are obtained by hydrolysis of the alkylated pyrazinones.
引用
收藏
页码：2809 / 2820
页数：12
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