Polymer-supported chiral sulfonamide catalyzed one-pot reduction of beta-keto nitriles: a practical synthesis of (R)-fluoxetine and (R)-duloxetine

Enantioselective reduction of beta-keto nitriles to optically active 1,3-amino alcohols has been carried out in one Step using an excess of borane-dimethyl sulfide complex as a reductant and a polymer-supported chiral sulfonamide as a catalyst with moderate to high enantioselectivity. The facile and enantioselective method to prepare optically active 1,3-amino alcohols to be converted into 3-aryloxy-3-arylpropyl imiiie-type antidepressant drugs (R)-fluoxetine, and (R)-duloxetine is also reported. (C) 2005 Elsevier Ltd. All rights reserved.