Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates

Benoit Cardinal-David, Dustin E. A. Raup and Karl A. Scheidt*

*Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, Evanston, Illinois 60208, Email: scheidtnorthwestern.edu

B. Cardinal-David, D. E. A. Raup, K. A. Scheidt, J. Am. Chem. Soc., 2010, 132, 5345-5347.

DOI: 10.1021/ja910666n

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Abstract

N-Heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. The presence of Ti(OiPr)₄ as Lewis acid enables an efficient substrate preorganization, which translates into high levels of diastereoselectivity.

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Key Words

Cyclopentenes

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ID: J48-Y2010-1000