Synfacts 2007(7): 0721-0721  
DOI: 10.1055/s-2007-968616
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Mediated Conjugate Reduction of Prochiral Sulfones

Contributor(s): Mark Lautens, Michael Langer
T. Llamas, R. Gómez Arrayás, J. C. Carretero*
Universidad Autónoma de Madrid, Spain
Further Information

Publication History

Publication Date:
22 June 2007 (online)

Significance

The paper describes a mild method to generate synthetically useful compounds with a stereocenter in the β-position of a sulfone. The R groups in β -position can be aliphatic or aromatic (with EWG and EDG substituents). The reduction is carried out in a highly stereoselective fashion to generate the products in high yield and high selectivity. The sulfone group can be easily converted into other functional groups after reduction without erosion of the optical purity. For instance Julia-Kocienski olefination gives access to compounds with an allylic stereocenter. For a recent short review on copper-mediated conjugate reductions, see: S. Rendler, M. Oestreich Angew. Chem. 2007, 119, 504-510.