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Issue 10, 2011
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Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

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Abstract

A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21 : 1 diastereoselectivity and up to 99% enantioselectivity.

Graphical abstract: Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

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Publication details

The article was received on 24 Jun 2011, accepted on 12 Jul 2011 and first published on 03 Aug 2011


Article type: Edge Article
DOI: 10.1039/C1SC00390A
Chem. Sci., 2011,2, 2035-2039

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    Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

    M. Ding, F. Zhou, Y. Liu, C. Wang, X. Zhao and J. Zhou, Chem. Sci., 2011, 2, 2035
    DOI: 10.1039/C1SC00390A

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