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Issue 7, 2013
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Cation-directed enantioselective synthesis of quaternary-substituted indolenines

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Abstract

An asymmetric method for the synthesis of quaternary-substituted indolenines via a 5-endo-dig cyclization of an α-cyanocarbanion onto an isonitrile has been developed. This transformation relies on Brønsted acid activation of the isonitrile functional group under asymmetric phase transfer conditions in the presence of a Brønsted base. Good to excellent levels of enantioselectivity were obtained (85 : 15 to 96 : 4 e.r., 18 examples) using a bespoke bifunctional catalyst. Enantioenriched indolenines produced in this process can be intercepted by nucleophilic species with high levels of diastereoselectivity to generate complex indoline frameworks. This process offers a general asymmetric approach to reactions involving the isonitrile functional group.

Graphical abstract: Cation-directed enantioselective synthesis of quaternary-substituted indolenines

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Publication details

The article was received on 01 Mar 2013, accepted on 28 Apr 2013 and first published on 10 May 2013


Article type: Edge Article
DOI: 10.1039/C3SC50592H
Citation: Chem. Sci., 2013,4, 2907-2911
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    Cation-directed enantioselective synthesis of quaternary-substituted indolenines

    M. Li, P. A. Woods and M. D. Smith, Chem. Sci., 2013, 4, 2907
    DOI: 10.1039/C3SC50592H

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