Stereoselective synthesis of cis- and trans-4-acyl-β-lactams from vicinal diketones and ketoaldehydes  

作　　者：WANG ZhiXin XU JiaXi 

机构地区：[1]State Key Laboratory of Chemical Resource Engineering,Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China

出　　处：《Science China Chemistry》2011年第11期1711-1717,共7页中国科学(化学英文版)

基　　金：the support from the National Natural Science Foundation of China (20972013 and 20772005);Beijing Natural Science Foundation (2092022);the Fundamental Research Funds for the Central Universities (ZZ1020);the Doctoral Fund of Ministry of Edu-cation of China (200800100010)

摘　　要：4-Acyl-β-lactams are important synthetic intermediates in both pharmaceutical and organic chemistry. Cis- and trans-4-acyl-β- lactams were synthesized stereoselectively from vicinal diketones via the formation of bulky and less bulky diimines as key intermediates, respectively. The diimines reacted with acyl chloride in the presence of triethylamine to give rise to the corre- sponding 4-imino-β-lactams, which were further hydrolyzed to afford 4-acyl-β-lactams. The cis- and trans selectivity is de- pended on the steric hindrance of the imine N-substituents. A series of cis-4-acyl-β-lactams were synthesized from vicinal ketoaldehydes via the formation of their monoimines and diimines as intermediates. Pyruvic aldehyde produced cis-4-acetyl-β- lactams and cis-4-formyl-β-lactams, respectively, through the reactions of its monoimine and diimine with acyl chlorides. Phenylglyoxal generated cis-4-benzoyl-β-lactams via its monoaldimine.4-Acyl-β-lactams are important synthetic intermediates in both pharmaceutical and organic chemistry. Cis- and trans-4-acyl-β- lactams were synthesized stereoselectively from vicinal diketones via the formation of bulky and less bulky diimines as key intermediates, respectively. The diimines reacted with acyl chloride in the presence of triethylamine-to give rise to the corresponding 4-imino-β-lactams, which were further hydrolyzed to afford 4-acyl-β-lactams. The cis- and trans selectivity is depended on the steric hindrance of the imine N-substituents. A series of cis-4-acyl-β-lactams were synthesized from vicinal ketoaldehydes via the formation of their monoimines and diimines as intermediates. Pyruvic aldehyde produced cis-4-acetyl-β- lactams and cis-4-formyl-β-lactams, respectively, through the reactions of its monoimine and diimine with acyl chlorides. Phenylglyoxal generated cis-4-benzoyl-β-lactams via its monoaldimine.

关 键 词：4-acyl-β-lactam DIIMINE DIKETONE imine ketoaldehyde Β-LACTAM stereoselectivity 

分 类 号：O623.52[理学—有机化学]