Electrochemical Deallylation of α-Allyl Cyclic Amines and Synthesis of Optically Active Quaternary Cyclic Amino Acids

被引：21

作者：

Kirira, Peter G. ^{[1
]}

Kuriyama, Masami ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 13期

关键词：

alkylation; allylation; amino acids; diastereoselectivity; electrochemical oxidation; N-ACYLIMINIUM IONS; INTERMOLECULAR ADDITION-REACTIONS; ELECTROORGANIC CHEMISTRY; ANODIC-OXIDATION; STEREOSELECTIVE-SYNTHESIS; 1,3-ASYMMETRIC INDUCTION; ASYMMETRIC-SYNTHESIS; CONVENIENT METHOD; RECENT PROGRESS; L-LYSINE;

D O I：

10.1002/chem.200903512

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electrochemical oxidation of alpha-allylated and alpha-benzylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding alpha-methoxylated products with up to 76% yield. Ease of oxidation was affected by the type of electrode, the size of cyclic amine, and the nature of the protecting group. This method was successfully applied to the synthesis of optically active N-acylated a-alkyl-a-amino acid esters with up to 99% ee.

引用

页码：3970 / 3982

页数：13

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