New palladium-mediated reactions for asymmetric organic synthesis

ORGN 210

Helena C. Malinakova, Department of Chemistry, Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, 2010 Malott Hall, Lawrence, KS 66045
Palladium-catalyzed carbon-carbon bond-forming reactions became recognized as powerful tools in organic synthesis. Aiming to design new synthetic pathways, as well as to elucidate the mechanism of stereoinduction, we have been exploring synthesis and reactivity of new types of organopalladium complexes. Stable chiral nonracemic palladacycles featuring a metal-bonded stereogenic carbon have been synthesized, and their reactions with diverse unsaturated building blocks providing nonracemic heterocycles, e.g. 2H-1-benzopyrans and 1,2-dihydroquinolines, have been demonstrated. Our studies on metal-mediated allylation reactions culminated in the development of a new, regio- and diastereoselective method for a palladium-catalyzed coupling of boronic acids, allenes and aldehydes yielding highly substituted homoallylic alcohols in one step. Unsymmetrical bis-p-allylpalladium(II) complexes of an unprecedented complexity are believed to operate as catalytic intermediates in this multi-component coupling protocol. In this lecture, most recent advances of our research program will be discussed.

 

Women in Organic Synthesis
8:45 AM-12:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Ballroom A, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004