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  

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

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作  者:邱丽华 沈宗旋 陈五红 张勇 张雅文 

机构地区:[1]Department of Chemistry and Chemical Engineering, Suzhou University

出  处:《Chinese Journal of Chemistry》2003年第8期1098-1100,共3页中国化学(英文版)

基  金:theNaturalScienceFoundationofJiangsuEducationOffice (No .0 1KJB15 0 0 0 2 )

摘  要:Cyclodipeptide (3 S,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 NaBH 4 BF 3 in DME gave the (2 S,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.Cyclodipeptide (3 S,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 NaBH 4 BF 3 in DME gave the (2 S,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.

关 键 词:cyclodipeptide piperazine  1 4  dione C    2  symmetric preparation 

分 类 号:O625[理学—有机化学]

 

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