ORGN 647 |
Rh-catalyzed highly enantioselective intramolecular Alder-ene reaction for the formation of functionalized cyclopentanes and cyclopentanones
| Xumu Zhang1, Minsheng He1, Aiwen Lei1, and Gao Shang2. (1) Department of Chemistry, Pennsylvania State University, 152 Davey Lab, University Park, PA 16802, (2) Department of Chemistry, The Pennsylvania State University, 102 Chemistry Building, University Park, PA 16802 |
| Cyclopentanes and cyclopentanones are among the basic skeletons of organic molecules. Since numerous natural products and biologically active molecules contain these structure motifs, functionalized cyclopentanes and cyclopentanones are important building blocks for the construction of complex molecules. The transition metal-catalyzed cycloisomerization of enynes has been extensively studied as an elegant method to construct heterocyclic and carbocyclic compounds. However, the asymmetric version of the reaction has not been fully developed. Recently, we successful achieved highly enantioselective Rh-catalyzed cycloisomerization of enynes. Syntheses of polyfunctional cyclopentanes and cyclopentanones were performed and high enantioselectivity ( >99% ee ) and high yield were achieved. Asymmetric synthesis of natural product (+)-methyl dihydrojasmonate was performed. Some mechanistic insights are provided in this system via NMR studies. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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