Asymmetric palladium-catalyzed C-O and C-N bond formations using non-racemic allylic hydroxy phosphonates

ORGN 782

Christopher D. Spilling, cspill@umsl.edu, Anyu He, and Anchalee Thanavaro. Department of Chemistry and Biochemistry, University of Missouri-St. Louis, 315 Benton Hall, One University Boulevard, St. Louis, MO 63121
Non-racemic allylic hydroxy phosphonates are formed by asymmetric phosphonylation of aldehydes or cross-metathesis of an alkene and the acrolein-derived phosphonate. These hydroxy phosphonates display some of the rich chemistry associated with allylic alcohols. However, the steric and electronic influence of the phosphorus moiety can enhance the regio-and stereochemical outcome of the reaction. Recent results in the inter- and intra-molecular addition of nitrogen and oxygen nucleophiles and application in the synthesis of heterocycles will be described.