Synlett 2014; 25(4): 457-460
DOI: 10.1055/s-0033-1340318
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© Georg Thieme Verlag Stuttgart · New York

Asymmetric Friedel–Crafts Alkylation Reaction in the Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters

Hao Wu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320544   Email: yxjia@zjut.edu.cn
,
Ren-Rong Liu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320544   Email: yxjia@zjut.edu.cn
,
Yi-Xia Jia*
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320544   Email: yxjia@zjut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 17 October 2013

Accepted after revision: 31 October 2013

Publication Date:
10 December 2013 (online)

Abstract

Construction of all-carbon quaternary stereocenter by asymmetric Friedel–Crafts alkylation reaction remains a significant challenge. By the introduction of CF3 group at the β-position of nitroalkene, a highly enantioselective Friedel–Crafts reaction of indoles with β-CF3-β-substituted nitroalkenes was achieved using Ni(ClO4)2-bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereogenic centers in good yields and excellent enantio­selectivities.

 
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