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

页码：2809 / 2820

页数：12

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