Tuesday, May 20, 2008 - 11:10 AM
Medical Arts Building, Rm M-134 (Queensborough Community College)
381

Tandem Asymmetric C-C Bond-Forming Reactions

Patrick J. Walsh, University of Pennsylvania, Philadelphia, PA

We have developed several highly enantio- and diastereoselective one-pot methods for the efficient synthesis of synthetically useful cyclopropyl alcohols. Our methods take advantage of a highly enantioselective C-C bond-forming reaction to set the initial chirality. The resulting allylic zinc alkoxide intermediate is then subjected to either cyclopropanation or halocyclopropanation. This method allows generation of up to 4 stereogenic centers in a one-pot procedure from achiral precursors.