Download PDF
Synfacts 2009(3): 0293-0293  
DOI: 10.1055/s-0028-1087747
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Molybdenum-Catalyzed Enantioselective Alkene Metathesis

Contributor(s): Mark Lautens, Jacki Kitching
S. J. Malcolmson, S. J. Meek, E. S. Sattely, R. R. Schrock, A. H. Hoveyda*
Boston College, Chestnut Hill and Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
19 February 2009 (online)

    Permissions and Reprints

Significance

The present paper discusses novel molybdenum-based chiral catalysts that initiate enantioselective ring-closing metathesis (RCM) ­reactions. These configurationally stable catalysts are stereogenic-at-metal and bear only monodentate ligands. The utility of these catalysts is demonstrated in the enantioselective synthesis of the Aspidosperma alkaloid quebrachamine. The RCM reaction proceeds in 84% yield (96% ee) and could not be promoted by any of the previously reported chiral molybdenum- or ruthenium-based catalysts.