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Silyl Ketene Imines: Highly Versatile Nucleophiles for Catalytic, Asymmetric Synthesis

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 51, Issue 40, Pages 9980-9992

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201202139

Keywords

asymmetric catalysis; cyanides; silanes; synthetic methods; umpolung

Funding

  1. NIGMS NIH HHS [R01 GM085235] Funding Source: Medline

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This Minireview provides an overview on the development of silyl ketene imines and their recent applications in catalytic, enantioselective reactions. The unique structure of the ketene imine allows a diverse range of reactivity patterns and provides solutions to existing challenges in the enantioselective construction of quaternary stereogenic carbon centers and cross-benzoin adducts. A variety of reactions for which silyl ketene imines have been applied are presented with an overall goal of inspiring new uses for these underutilized nucleophiles.

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