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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

                Users may view, print, copy, download and text and data- mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms

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

                Chemistry

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