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Synthesis 2015; 47(07): 1024-1031
DOI: 10.1055/s-0034-1379943
DOI: 10.1055/s-0034-1379943
paper
Organocatalytic Asymmetric Domino Michael/Henry Reaction of Indolin-3-ones with o-Formyl-β-nitrostyrenes
Further Information
Publication History
Received: 01 December 2014
Accepted: 02 December 2014
Publication Date:
05 January 2015 (online)
Abstract
A highly diastereo- and enantioselective domino Michael/ Henry reaction of 1-acetylindolin-3-ones with o-formyl-(E)-β-nitrostyrenes catalyzed by low loading of a quinine-derived amine-squaramide provides the corresponding indolin-3-one derivatives bearing four adjacent stereogenic centers in good to high yields and with excellent stereoselectivities.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379943.
- Supporting Information
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For recent reviews on the asymmetric synthesis of 2-oxindole derivatives, see:
For selected reviews on organocatalytic domino reactions, see:
For the synthesis of enantiopure indolin-3-ones via addition reactions to the C=N bond of 2-substituted 3H-indol-3-ones or their analogues, see:
For the synthesis of enantiopure indolin-3-one derivatives via addition reactions of indolin-3-ones to various acceptors, see:
For excellent reviews on squaramide catalysts, see:
For recent examples from our group, see: