Diazaphospholene Precatalysts for Imine and Conjugate Reductions

The first examples of 1,3,2-diazaphospholene-catalyzed imine reduction and conjugate reduction reactions are reported. This approach employs readily synthesized alkoxydiazaphospholene precatalysts that can be handled in open air. Reduction of substrates containing Lewis basic functionality, isolated unsaturation, and protic functional groups was accomplished. The synthetic utility of this approach is demonstrated by the synthesis of the important antiparkinson medicine rasagiline and the natural product zingerone.