Stereoselective radical and Heck cyclizations of axially chiral anilides with transfer of axial chirality to newly formed stereocenters

ORGN 106

Andre J. B. Lapierre and Dennis Curran. Chevron Science Center - Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260
Axially chiral anilides exhibit slow rotation about the N–aryl bond such that conformationally stable enantiomers can be chromatographically isolated and manipulated at room temperature. When submitted to radical or Heck cyclization conditions enantioenriched oxindole and dihydroindole products are generated with faithful transfer of axial chirality to the newly formed stereocenter.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 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