Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams

NA White, DA DiRocco, T Rovis

Index: White, Nicholas A.; Dirocco, Daniel A.; Rovis, Tomislav Journal of the American Chemical Society, 2013 , vol. 135, # 23 p. 8504 - 8507

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Citation Number: 46

Abstract

An asymmetric intermolecular reaction between enals and nitroalkenes to yield δ-nitroesters has been developed, catalyzed by a novel chiral N-heterocyclic carbene. Key to this work was the development of a catalyst that favors the δ-nitroester pathway over the established Stetter pathway. The reaction proceeds in high stereoselectivity and affords the previously unreported syn diastereomer. We also report an operationally facile two-step, one-pot ...