Cu(I)-catalyzed highly exo-selective and enantioselective [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes

ORGN 93

Wenzhong Gao, wug1@psu.edu, Chemistry Department, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802, Malati Raghunath, malati@psu.edu, Department of Chemistry, Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802, and Xumu Zhang, xumu@chem.psu.edu, Department of Chemistry, The Pennsylvania State University, 104 Chemistry Research Building, University Park, State College, PA 16802.
1,3-Dipolar cycloaddition is one of the most powerful methods for construction of highly substituted five-membered heterocycles. To our knowledge, highly exo- and enantioselective 1,3-dipolar cycloaddition reaction of azomethine ylides have not yet been developed. Herein, we would like to present our investigation on the Cu(I)/P,N-ligand catalyzed [3+2] cycloaddition of N-metalated azomethine ylides with deficient olefins. The reaction of different dipolarophiles such as t-butyl acrylate, methyl acrylate, ethyl acrylate and dimethyl maleate proceeded in both excellent exo- selectivities and high yields, and up to 98% enantiometric excess was observed.

 

New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005