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Issue 61, 2017
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Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives

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Abstract

A Lewis acid catalyzed [3+4]-annulation reaction between cyclopropane 1,1-diesters and anthranils has been developed. This annulation consists of a reaction sequence involving ring-opening/aromatization/nucleophilic addition. Thereinto, aromatization is the driving force for this annulation. Using this reaction, a series of 8-oxa-1-azabicyclo[3.2.1]octanes can be prepared conveniently with excellent diastereoselectivity.

Graphical abstract: Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives

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Publication details

The article was received on 01 Jun 2017, accepted on 04 Jul 2017 and first published on 14 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC04239F
Citation: Chem. Commun., 2017,53, 8521-8524
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    Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives

    Z. Wang, H. Zhang, D. Wang, P. Xu and Y. Luo, Chem. Commun., 2017, 53, 8521
    DOI: 10.1039/C7CC04239F

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