Wednesday, 31 May 2006 - 9:40 AM
Regency Ballroom D (Hyatt Regency Milwaukee)
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Stereoselective Synthesis of Chiral Biaryls through Rhodium-Catalyzed [2+2+2] Cycloaddtion of Chiral Ynamides with 1,6-Diynes

Jossian Oppenheimer, Michael R. Tracey, and Richard P. Hsung. University of Wisconsin, Madison, WI

Stereoselective Synthesis of Chiral Biaryls through Rhodium-Catalyzed [2+2+2] Cycloaddtion of Chiral Ynamides with 1,6-Diynes

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 chirala ynamides.

Scheme 1.


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