A convenient approach to the enantiopure (1S, 2S, 4S, 5S)- and (1R, 2S, 4R, 5S)-2,5-bis(phenylmethyl)-1, 4-diazabicyclo[2.2.2]-octane

被引：0

作者：

Qiu, LH ^{[1
]}

Shen, ZX ^{[1
]}

Chen, WH ^{[1
]}

Zhang, Y ^{[1
]}

Zhang, YW ^{[1
]}

机构：

[1] Suzhou Univ, Dept Chem & Chem Engn, Suzhou 215006, Jiangsu, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2003年 / 21卷 / 08期

关键词：

cyclodipeptide; piperazine-1,4-dione; C-2-symmetric; preparation;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclodipeptide (3S; 6S)-bis (phenylmethyl) piperazine-2, 5-dione was prepared in high yield by heating phenylalanine methyl ester in toluene under reflux. The reduction of this cyclodipeptide with sodium NaBH4-BF3 in DME gave the (2S, 5S)-bis (phenylmethyl) piperazine, which, on heating with ethylene bromide and triethylamine, afforded the title compounds. This method was proved to be generally applicable to the synthesis of C-2-symmetric 2, 5-disubstituted-1, 4-diazabicyclo [2.2.2] octane from the corresponding natural or unnatural amino acid esters.

引用

页码：1098 / 1100

页数：3

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