Rhodium(I)-catalyzed [2+2+2] cycloadditions of ynamides in the synthesis of amide-substituted chiral biaryls

ORGN 588

Jossian Oppenheimer, oppenheimer2@wisc.edu, Division of Pharmaceutical Sciences, The University of Wisconsin, 777 Highland Avenue, Madison, WI 53705-2222, Michael R. Tracey, Department of Chemistry, University of Minnesota, Smith and Kolthoff Halls, 207 Pleasant Street SE, Minneapolis, MN 55455-0431, and Richard P. Hsung, rphsung@pharmacy.wisc.edu, Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin-Madison, 777 Highland Ave., Rennebohm Hall, Madison, WI 53705-2222.
Cycloadditions and related annulations represent powerful synthetic methods for constructing aromatic and heteroaromatic systems. Relatively less attention has been given to syntheses of chiral biaryls. Ynamides have proven to be a versatile organic building block in a diverse array of new methodologies. However, cycloaddition employing chiral ynamides en route to the synthesis of chiral biaryls has not been reported (Scheme 1). We communicate here a stereoselective [2+2+2] cycloaddition of chiral ynamides.

Scheme 1.

 

Metal-Mediated Reactions and Syntheses
1:00 PM-4:20 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E350, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007