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NHC-Catalyzed Addition of Homoenolate Equivalents to Unsaturated Keto Esters
D. T. Cohen, B. Cardinal-David, K. A. Scheidt*
Northwestern University, Evanston, USA
18 March 2011 (online)
A N-heterocyclic carbene catalyzed addition of homoenolate equivalents derived from enals 1 to unsaturated β,γ-unsaturated α-keto esters 2 has been reported. Lewis acidic Ti(Oi-Pr)4 was compatible with NHC catalysis and crucial for the formation of the desired products. N-heterocyclic carbene precatalyst 3 delivered substituted cyclopentanes 4 possessing four contiguous stereocenters in moderate to good yields with high diastereoselectivity and excellent enantioselectivity.