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

Graves, Christopher R.; Scheidt, Karl A.; Nguyen, SonBinh T.

doi:10.1021/ol060110w.s001

Enantioselective MSPV Reduction of Ketimines Using 2-Propanol and (BINOL)Al^III

journal contribution

posted on 2006-03-16, 00:00 authored 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)Al^III/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.