Synfacts 2007(8): 0842-0842  
DOI: 10.1055/s-2007-968769
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Reduction of Nitroalkene Isomers by Base-Induced Equilibration

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
C. Czekelius, E. M. Carreira*
ETH Zürich, Switzerland
Further Information

Publication History

Publication Date:
24 July 2007 (online)

Significance

The authors report a highly practical and efficient reduction of isomeric mixtures of 1a and 1b to give the corresponding chiral nitro compound in high yield and enantiomeric excess. Prior to this work, the authors reported the asymmetric reduction of nitroalkene 1a (Angew. Chem. Int. Ed. 2003, 42, 4793). However, in the presence of adventitious base or after prolonged storage 1a isomerizes to give 1b. Addition of n-Bu4OH to the reaction mixture converts 1b into 1a without any loss of catalytic activity.