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      Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization.

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          Abstract

          The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Brønsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.

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          Author and article information

          Journal
          J. Am. Chem. Soc.
          Journal of the American Chemical Society
          1520-5126
          0002-7863
          Nov 27 2013
          : 135
          : 47
          Affiliations
          [1 ] Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
          Article
          10.1021/ja4100595
          24215561

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