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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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Supplementary files

Article information


Submitted
16 Jun 2015
Accepted
23 Jul 2015
First published
30 Jul 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 6086-6090
Article type
Edge Article
Author version available

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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