Copper-catalyzed asymmetric cycloadditions to form dihydrofurans

ORGN 599

Sunghee Son, sunghee@mit.edu and Gregory C. Fu, gcf@mit.edu. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139
2,3-Dihydrofurans can not only be found in biologically active compounds but also serve as useful synthetic intermediates. Despite their importance, few catalytic asymmetric methods have been developed for their synthesis. Herein, we report copper-catalyzed asymmetric [4+1] cycloadditions of enones with diazoacetates. This method produces highly substituted 2,3-dihydrofurans in good yield, dr, and ee, and these products can be derivatized to other useful molecules. Deoxy-C-nucleosides were synthesized with high efficiency and selectivity.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007