title: Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated D-galactosyl)benzylideneamines and ring-opening reactions with p-toluenethiol.
abstract: N-Galactosyl aziridines were synthesized via BF3·OEt2 promoted addition of carbenes generated from diazocarbonyl compounds with O-pivaloylated β-D-galactosylimines in good yields and high diastereoselectivity. The ring-opening reactions with p-toluenethiol of the aziridines provided enantiometrically pure β-S-substituted phenylalanine derivatives in a highly regioselective manner.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, People's Republic of China. xbmeng@bjmu.edu.cn zjli@bjmu.edu.cn.
authors.forename: Yizhou
authors.initials: Y
authors.lastname: Zhao
authors.forename: Gang
authors.initials: G
authors.lastname: Wang
authors.forename: Shanshan
authors.initials: S
authors.lastname: Zhou
authors.forename: Zhongjun
authors.initials: Z
authors.lastname: Li
authors.forename: Xiangbao
authors.initials: X
authors.lastname: Meng
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D005690:Galactose / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D001388:Aziridines; D001391:Azo Compounds; D001597:Benzylidene Compounds; D013438:Sulfhydryl Compounds; C540257:4-methylbenzenethiol; D005690:Galactose