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Issue 11, 2011
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Employing homoenolates generated by NHC catalysis in carbon–carbon bond-forming reactions: state of the art

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Abstract

Homoenolate is a reactive intermediate that possesses an anionic or nucleophilic carbon β to a carbonyl group or its synthetic equivalent. The recent discovery that homoenolates can be generated from α,β-unsaturated aldehydesviaN-Heterocyclic Carbene (NHC) catalysis has led to the development of a number of new reactions. A majority of such reactions include the use of carbon-based electrophiles, such as aldehydes, imines, enones, dienones etc. resulting in the formation of a variety of annulated as well as acyclic products. The easy availability of chiral NHCs has allowed the development of very efficient enantioselective variants of these reactions also. The tolerance showed by NHCs towards magnesium and titanium based Lewis acids has been exploited in the invention of cooperative catalytic processes. This tutorial review focuses on these and other types of homoenolate reactions reported recently, and in the process, updates the previous account published in 2008 in this journal.

Graphical abstract: Employing homoenolates generated by NHC catalysis in carbon–carbon bond-forming reactions: state of the art

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Publication details

The article was received on 25 May 2011 and first published on 20 Jul 2011


Article type: Tutorial Review
DOI: 10.1039/C1CS15139H
Citation: Chem. Soc. Rev., 2011,40, 5336-5346

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    Employing homoenolates generated by NHC catalysis in carbon–carbon bond-forming reactions: state of the art

    V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose and V. Sreekumar, Chem. Soc. Rev., 2011, 40, 5336
    DOI: 10.1039/C1CS15139H

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