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Issue 11, 2015
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Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

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Abstract

A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (∼€70 kg−1) as the stoichiometric reductant. Base-catalyzed Pudovik addition and phosphonate/phosphate rearrangement achieved polarity inversion on the isatin, and the derived carbanions were trapped by aldehydes with subsequent dialkoxyphosphinyl migration. Chiral iminophosphoranes were used as basic catalysts to achieve high diastereo- and enantioselectivities with excellent yields.

Graphical abstract: Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

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Publication details

The article was received on 16 Jun 2015, accepted on 23 Jul 2015 and first published on 30 Jul 2015


Article type: Edge Article
DOI: 10.1039/C5SC02170G
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Citation: Chem. Sci., 2015,6, 6086-6090
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    Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

    M. A. Horwitz, N. Tanaka, T. Yokosaka, D. Uraguchi, J. S. Johnson and T. Ooi, Chem. Sci., 2015, 6, 6086
    DOI: 10.1039/C5SC02170G

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