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Cooperative Catalysis by Carbenes and Lewis Acids in a Highly Stereoselective Route to γ-Lactams

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      Abstract

      Enzymes are a continuing source of inspiration for the design of new chemical reactions that proceed with efficiency, high selectivity and minimal waste. In many biochemical processes, different catalytic species, such as Lewis acids and bases, are involved in precisely orchestrated interactions to activate reactants simultaneously or sequentially. Employing this type of cooperative catalysis, in which two or more catalytic cycles operate concurrently to achieve one overall transformation, has great potential to enhance known reactivity and drive the development of new chemical reactions with high value. In this disclosure, a cooperative N-heterocyclic carbene/Lewis acid catalytic system promotes the addition of homoenolate equivalents to hydrazones generating highly substituted γ-lactams in moderate to good yields and high levels of diastereo- and enantioselectivity.

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      Most cited references 65

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      Organocatalysis by N-heterocyclic carbenes.

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        N-heterocyclic carbenes in late transition metal catalysis.

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          Frustrated Lewis Pairs: Metal-free Hydrogen Activation and More

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            Author and article information

            Affiliations
            Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208
            Author notes
            Correspondence and requests for materials should be addressed to Karl A. Scheidt ( scheidt@ 123456northwestern.edu )
            Journal
            101499734
            35773
            Nat Chem
            Nature chemistry
            1755-4330
            1755-4349
            13 July 2010
            18 July 2010
            September 2010
            1 March 2011
            : 2
            : 9
            : 766-771
            2928160
            20729898
            10.1038/nchem.727
            nihpa207933

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            Funding
            Funded by: National Institute of General Medical Sciences : NIGMS
            Award ID: R01 GM073072-04 ||GM
            Categories
            Article

            Chemistry

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