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学科主题: 药学
题名:
InCl3-catalyzed asymmetric aza-Friedel-Crafts reaction of indoles with imines generated from O-pivaloylated beta-D-galactosylamine
作者: 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
发表日期: 2010-08-16
DOI: 10.1016/j.carres.2010.05.025
卷: 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
所属项目编号: 20602001 ; 2009ZX09501-011
项目资助者: National Natural Science Foundation of China (NSFC) ; The State New Drug Innovation (the Ministry of Science and Technology of China)
WOS记录号: WOS:000280905200008
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/59063
Appears in Collections:北京大学药学院_化学生物学系_期刊论文

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作者单位: Peking Univ, State Key Lab Nat & Biomimet Drugs, Dept Biol Chem, Sch Pharmaceut Sci, Beijing 100191, Peoples R China

Recommended Citation:
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.
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