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Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated D-galactosyl) benzylideneamines and ring-opening reactions with p-toluenethiol
Zhao, Yizhou1; Wang, Gang1; Zhou, Shanshan1; Li, Zhongjun1; Meng, Xiangbao1
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2014
DOI10.1039/c4ob00443d
12期:21页:3362-3365
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
资助者National Natural Science Foundation of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Basic Research Program of China
研究领域[WOS]Chemistry
关键词[WOS]MANNICH-MICHAEL REACTIONS ; ASYMMETRIC-SYNTHESIS ; STEREOSELECTIVE-SYNTHESIS ; CHIRAL TEMPLATES ; UGI-SYNTHESIS ; CARBOHYDRATE TEMPLATES ; CATALYZED SYNTHESIS ; LEWIS-ACID ; DERIVATIVES ; ALKALOIDS
英文摘要

N-Galactosyl aziridines were synthesized via BF3 center dot OEt2 promoted addition of carbenes generated from diazocarbonyl compounds with O-pivaloylated beta-D-galactosylimines in good yields and high diastereoselectivity. The ring-opening reactions with p-toluenethiol of the aziridines provided enantiometrically pure beta-S-substituted phenylalanine derivatives in a highly regioselective manner.

语种英语
所属项目编号21072017 ; 2012CB822100
资助者National Natural Science Foundation of China ; National Basic Research Program of China ; National Natural Science Foundation of China ; National Basic Research Program of China
WOS记录号WOS:000336023400008
引用统计
被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/52910
专题北京大学药学院
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Zhao, Yizhou,Wang, Gang,Zhou, Shanshan,et al. Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated D-galactosyl) benzylideneamines and ring-opening reactions with p-toluenethiol[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2014,12(21):3362-3365.
APA Zhao, Yizhou,Wang, Gang,Zhou, Shanshan,Li, Zhongjun,&Meng, Xiangbao.(2014).Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated D-galactosyl) benzylideneamines and ring-opening reactions with p-toluenethiol.ORGANIC & BIOMOLECULAR CHEMISTRY,12(21),3362-3365.
MLA Zhao, Yizhou,et al."Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated D-galactosyl) benzylideneamines and ring-opening reactions with p-toluenethiol".ORGANIC & BIOMOLECULAR CHEMISTRY 12.21(2014):3362-3365.
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