Palladium-catalyzed cascade annulation of unactivated secondary halides

ORGN 272

Alena Rudolph, arudolph@chem.utoronto.ca, Nils Rackelmann, and Mark Lautens, mlautens@chem.utoronto.ca. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada
Our group has explored the synthesis of bi- and tricyclic heterocycles utilizing a palladium-catalyzed ortho-alkylation domino reaction sequence. Application of this novel reaction sequence to secondary alkyl halides will be presented. The use of enantioenriched secondary halides leads to the corresponding enantioenriched fused heterocycles, allowing for mechanistic insight into the stereochemistry of the ortho-alkylation step.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Monday, 11 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006