Synfacts 2008(8): 0833-0833  
DOI: 10.1055/s-2008-1077904
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ti-Catalyzed Radical Generation/Rh-Catalyzed Hydrogen Atom Transfer

Contributor(s): Mark Lautens, Praew Thansandote
A. Gansäuer*, C.-A. Fan, F. Piestert
Universität Bonn, Germany
Further Information

Publication History

Publication Date:
23 July 2008 (online)

Significance

The authors describe a creative sustainable radical reduction by coupling a Ti-catalyzed radical generation, from the opening of epoxides, with a hydrogen atom transfer from hydrogenated Wilkinson’s catalyst. Thus, hydrogen acts as the hydrogen atom source, which eliminates the use of undesirable stoichiometric metals such as stannanes and silanes. The reaction tolerates sensitive functionalities such as halides, tosylates, and esters. Enantioselective examples are shown with Kagan’s complex.