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Synfacts 2007(12): 1278-1278  
DOI: 10.1055/s-2007-991344
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Reductive Coupling of 1,3-Enynes to Glyoxalates

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
Y.-T. Hong, C.-W. Cho, E. Skucas, M. J. Krische*
University of Texas at Austin, USA and Kyungpook National University, Daegu, Korea
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Publikationsdatum:
22. November 2007 (online)

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Significance

In an earlier work the Krische lab has reported the coupling of 1,3-diynes to glyoxolates (C.-W. Cho, M. J. Krische Org. Lett. 2006, 8, 3873). The present study demonstrates the reductive coupling of 1,3-enynes to glyoxolates catalyzed by a cationic rhodium catalyst modified by ligand 1. Interestingly, commercially available chelating chiral phosphine ligands were uniformly unable to provide high levels of asymmetric induction. Lastly, the hydroxyl ester coupling products are elaborated to provide various useful chiral building blocks.