Issue 56, 2019

Stereospecific assembly of tetrahydroquinolines via tandem ring-opening/oxidative cyclization of donor–acceptor cyclopropanes with N-alkyl anilines

Abstract

An aerobic copper-catalyzed tandem reaction of N-alkyl anilines with donor–acceptor cyclopropanes is presented for the construction of tetrahydroquinolines via a sequential stereospecific ring opening and oxidative cyclization. The catalyst plays a dual role as a Lewis acid as well as being a redox catalyst. The use of air as an oxidant and the broad substrate scope are the important practical features.

Graphical abstract: Stereospecific assembly of tetrahydroquinolines via tandem ring-opening/oxidative cyclization of donor–acceptor cyclopropanes with N-alkyl anilines

Supplementary files

Article information

Article type
Communication
Submitted
25 May 2019
Accepted
11 Jun 2019
First published
12 Jun 2019

Chem. Commun., 2019,55, 8083-8086

Stereospecific assembly of tetrahydroquinolines via tandem ring-opening/oxidative cyclization of donor–acceptor cyclopropanes with N-alkyl anilines

B. Ketan Das, S. Pradhan and T. Punniyamurthy, Chem. Commun., 2019, 55, 8083 DOI: 10.1039/C9CC04042K

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