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Enantioselective MSPV Reduction of Ketimines Using 2-Propanol and (BINOL)AlIII

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journal contribution
posted on 16.03.2006, 00:00 by Christopher R. Graves, Karl A. Scheidt, SonBinh T. Nguyen
A highly enantioselective Meerwein−Schmidt−Ponndorf−Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)AlIII/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93−98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.