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.
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Matt R
MR
Adams
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Chieh-Hung
CH
Tien
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Blake S N
BSN
Huchenski
X-ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
Michael J
MJ
Ferguson
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Alexander W H
0000-0002-8997-3807
AWH
Speed
D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*
D001372:Aza Compounds; D007097:Imines; D009943:Organophosphorus Compounds; C013194:phospholenes
diazaphospholenes; homogeneous catalysis; imines; phosphorus hydrides; reduction