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Synfacts 2006(11): 1137-1137  
DOI: 10.1055/s-2006-949443
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Reductive Cyclization of Acetylenic Aldehydes via Hydrogenation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
J. U. Rhee, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

The group has further expanded its rhodium-catalyzed reactions under hydrogenation conditions. The use of Rh(cod)2OTf as catalyst with 2-naphthoic acid additive proved vital for obtaining high yields and high enantioselectivities of the five-membered ring products. (R)-Cl,MeO-BIPHEP was the chiral ligand of choice, while only 1 atm of H2 is needed for conversion. Various functional groups showed tolerability: ether, amide, and N-sulfonyl.