Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)Al(III).
[reaction: see text] 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.
Graves
Christopher R
CR
Department of Chemistry and Institute for Environmental Catalysis, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3313, USA.
Scheidt
Karl A
KA
Nguyen
Sonbinh T
ST