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Issue 2, 2015
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Enantioselective Friedel–Crafts reaction of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes

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Abstract

Using a Ni(ClO4)2–bisoxazoline complex as a catalyst, Friedel–Crafts alkylations of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes were carried out with high enantioselectivities (up to 91%) to give alkylated dihydroindoles bearing trifluoromethylated all-carbon quaternary stereocenters in good yields. The corresponding chiral C2 alkylated indoles were obtained with complete preservation of enantiomeric purity by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Graphical abstract: Enantioselective Friedel–Crafts reaction of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes

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Article information


Submitted
13 Oct 2014
Accepted
12 Dec 2014
First published
16 Dec 2014

Org. Chem. Front., 2015,2, 124-126
Article type
Research Article
Author version available

Enantioselective Friedel–Crafts reaction of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes

H. Wu, R. Liu, C. Shen, M. Zhang, J. Gao and Y. Jia, Org. Chem. Front., 2015, 2, 124
DOI: 10.1039/C4QO00265B

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