Issue 27, 2012
From the journal:

Chemical Communications

Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes†‡

Michele Retini,§a   Giulia Bergonzinia  and  Paolo Melchiorre*ab  

* Corresponding authors

a ICIQ - Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain
E-mail: pmelchiorre@iciq.es
Tel: +34 977920208

b ICREA - Institució Catalana de Recerca i Estudis Avançats, Pg. Lluís Companys 23, 08010 Barcelona, Spain

Abstract

The asymmetric Michael addition of dioxindoles to β-substituted nitroalkenes is reported. The bifunctional primary amine-thiourea A, by means of a non-covalent-based mode of catalysis, secures direct access to 3-substituted 3-hydroxyoxindole derivatives with high stereocontrol.

Graphical abstract: Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes

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Article information

DOI
https://doi.org/10.1039/C2CC30198A
Article type
Communication
Submitted
10 Jan 2012
Accepted
11 Feb 2012
First published
13 Feb 2012

Chem. Commun., 2012,48, 3336-3338

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Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes

M. Retini, G. Bergonzini and P. Melchiorre, Chem. Commun., 2012, 48, 3336 DOI: 10.1039/C2CC30198A

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