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InCl3-catalyzed asymmetric aza-Friedel-Crafts reaction of indoles with imines generated from O-pivaloylated beta-D-galactosylamine
Li, Bo-Yu; Li, Zhong-Jun; Meng, Xiang-Bao
关键词Asymmetric synthesis Aza-Friedel-Crafts reaction Carbohydrate auxiliary InCl3 3-Indolyl methanamine derivatives
刊名CARBOHYDRATE RESEARCH
2010-08-16
DOI10.1016/j.carres.2010.05.025
345期:12页:1708-1712
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biochemistry & Molecular Biology ; Chemistry, Applied ; Chemistry, Organic
研究领域[WOS]Biochemistry & Molecular Biology ; Chemistry
关键词[WOS]ALPHA-AMINO-ACIDS ; CHIRAL PHOSPHORIC-ACID ; CATALYTIC ENANTIOSELECTIVE ADDITION ; STEREOSELECTIVE STRECKER SYNTHESIS ; MANNICH-MICHAEL REACTIONS ; CARBOHYDRATE TEMPLATES ; UGI-SYNTHESIS ; DECAHYDROQUINOLINE ALKALOIDS ; PIPERIDINE ALKALOIDS ; DERIVATIVES
英文摘要

The highly diastereoselective InCl3-catalyzed aza-Friedel-Crafts reaction of substituted indoles with aldimines generated from Kunz′s amine was studied. The reaction afforded the desired product in good to high yields with up to >19:1 diastereoselective ratios. The O-pivaloylated beta-D-galactosyl moiety could not be cleaved under the traditional acidic conditions. It was removed successfully after unmasking of the O-pivaloyl groups using MeOH/NaOMe and treatment with HOAc/H2O subsequently, to yield the 3-indolyl aryl methanamine derivatives in high optical purity. (C) 2010 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000280905200008
引用统计
被引频次:12[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/400002259/59063
专题北京大学药学院_化学生物学系
作者单位Peking Univ, State Key Lab Nat & Biomimet Drugs, Dept Biol Chem, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Li, Bo-Yu,Li, Zhong-Jun,Meng, Xiang-Bao. InCl3-catalyzed asymmetric aza-Friedel-Crafts reaction of indoles with imines generated from O-pivaloylated beta-D-galactosylamine[J]. CARBOHYDRATE RESEARCH,2010,345(12):1708-1712.
APA Li, Bo-Yu,Li, Zhong-Jun,&Meng, Xiang-Bao.(2010).InCl3-catalyzed asymmetric aza-Friedel-Crafts reaction of indoles with imines generated from O-pivaloylated beta-D-galactosylamine.CARBOHYDRATE RESEARCH,345(12),1708-1712.
MLA Li, Bo-Yu,et al."InCl3-catalyzed asymmetric aza-Friedel-Crafts reaction of indoles with imines generated from O-pivaloylated beta-D-galactosylamine".CARBOHYDRATE RESEARCH 345.12(2010):1708-1712.
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