Chiral diamides as efficient catalytic precursors for the borane-mediated asymmetric reduction of prochiral ketones

Abstract

Chiral diamides [(2S)-5-oxo-2-(arylamino)carbonylpyrrolidines] derived from the abundantly available (S)-glutamic/(S)-pyroglutamic acids were successfully utilized as effective chiral catalytic precursors in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 91% enantiomeric purities. © 2007 Elsevier Ltd. All rights reserved.