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Synfacts 2011(4): 0437-0437  
DOI: 10.1055/s-0030-1259613
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

NHC-Catalyzed Addition of Homoenolate Equivalents to Unsaturated Keto Esters

Contributor(s): Benjamin List, Ilija Čorić
D. T. Cohen, B. Cardinal-David, K. A. Scheidt*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

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.