北京大学医学部机构知识库
Advanced  
IR@PKUHSC  > 北京大学药学院  > 化学生物学系  > 期刊论文
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

Files in This Item:

There are no files associated with this item.


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.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[Li, Bo-Yu]'s Articles
[Li, Zhong-Jun]'s Articles
[Meng, Xiang-Bao]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[Li, Bo-Yu]‘s Articles
[Li, Zhong-Jun]‘s Articles
[Meng, Xiang-Bao]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit

Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.

 

 

Valid XHTML 1.0!
Copyright © 2007-2017  北京大学医学部 - Feedback
Powered by CSpace