Double asymmetric induction in alkylation of the imines derived from(+)-camphor and (+)-or (-)-methyl glycinate

Acta Chimica Sinica ›› 1992, Vol. 50 ›› Issue (1): 89-95. Previous Articles Next Articles

Original Articles

N-(甘氨酸薄荷酯)-(+)-樟脑亚胺在烷基化反应中的双手性诱导效应

刘桂兰;周昌友;朴虎日;吴兰均;宓爱巧;蒋耀忠

中国科学院成都有机化学研究所

发布日期:1992-01-15

Double asymmetric induction in alkylation of the imines derived from(+)-camphor and (+)-or (-)-methyl glycinate

LIU GUILAN;ZHOU CHANGYOU;PIAO HURI;WU LANJUN;MI AIQIAO;JIANG YAOZHONG

Published:1992-01-15

Abstract

A double asym. induction effect has been observed in the alkylation of the imines derived from (+)-camphor and (+)- or (-)-menthyl glycinates. After hydrolysis of the alkylated intermediates, (R)-a-amino acids are obtained in 7.3-100% enantiomeric excess. Compared with the alkylation of the imine obtained from (+)-camphor of tert-Bu glycinate, the stereoselectivity of the alkylation of the (+)-menthyl imine is obviously enhanced. Using MeI as an alkylating reagent, (S)-alanine is obtained.

Key words: AMINO ACID, ALKYLATION, STEREOSELECTIVITY, GLYCINE, INDUCTIVE EFFECT

CLC Number:

O621

Cite this article

LIU GUILAN;ZHOU CHANGYOU;PIAO HURI;WU LANJUN;MI AIQIAO;JIANG YAOZHONG. Double asymmetric induction in alkylation of the imines derived from(+)-camphor and (+)-or (-)-methyl glycinate[J]. Acta Chimica Sinica, 1992, 50(1): 89-95.

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N-(甘氨酸薄荷酯)-(+)-樟脑亚胺在烷基化反应中的双手性诱导效应

Double asymmetric induction in alkylation of the imines derived from(+)-camphor and (+)-or (-)-methyl glycinate

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