A highly enantioselective synthesis of amide-substituted chiral biaryls through rhodium(I)-catalyzed asymmetric [2 + 2 + 2] cycloadditions of ynamides

ORGN 578

Jossian Oppenheimer, oppenheimer2@wisc.edu1, Whitney Johnson, wjohnson@chem.wisc.edu1, and Richard P. Hsung, rhsung@wisc.edu2. (1) Division of Pharmaceutical Sciences, The University of Wisconsin, 777 Highland Avenue, Madison, WI 53705-2222, (2) Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Rennebohm Hall, 777 Highland Avenue, Madison, WI 53705
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 achiral ynamides en route to the synthesis of chiral biaryls has not been reported. We communicate here a highly enantioselective [2+2+2] cycloaddition of achiral ynamides.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007