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Highly Enantioselective Reductive Cyclization of Acetylenic Aldehydes via Rhodium Catalyzed Asymmetric Hydrogenation

Jong Uk Rhee and Michael J. Krische*

*University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, Email: mkrischemail.utexas.edu

J. U. Rhee, M. J. Krische, J. Am. Chem. Soc., 2006, 128, 10674-10675.

DOI: 10.1021/ja0637954 (free Supporting Information)


Abstract

Catalytic hydrogenation of acetylenic aldehydes using a chirally modified cationic rhodium catalysts enables highly enantioselective reductive cyclization to afford cyclic allylic alcohols. Using an achiral hydrogenation catalyst, some chiral racemic acetylenic aldehydes engage in highly syn-diastereoselective reductive cyclizations.

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Key Words

Pyrrolidines, γ-Lactams, Cyclic Ethers, Allylic Alcohols


ID: J48-Y2006-2650