Synfacts 2006(4): 0344-0344  
DOI: 10.1055/s-2006-934335
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Hydrovinylation of 1,3-Dienes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
A. Zhang, T. V. RajanBabu*
Ohio State University, USA
Further Information

Publication History

Publication Date:
24 March 2006 (online)

Significance

Although the asymmetric hydrovinylation of 1,3-cyclohexadiene has been reported, the use of a complex azaphospholene ligand or the use of Et2AlCl is necessary. This protocol does not require the highly Lewis-acidic Et2AlCl and uses the simple ligand 1. While a major portion of this report pertains to the hydrovinylation of va­rious 1,3-dienes in a racemic, but regioselective manner, the authors do include a few asymmetric variants. All reactions give high conversion (>99% in most cases) and very high regioselectivity (>95% in most cases).