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N-Heterocyclic Carbene-Catalyzed Activation of α-Chloroaldehydes: Asymmetric Synthesis of 5-Cyano-Substituted Dihydropyranones

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An N-heterocyclic carbene (NHC)-catalyzed asymmetric [4+2] annulation of ( E )-2-benzoyl-3-phenylacrylonitriles with α-chloroaldehydes has been developed. The protocol leads to 5-cyano-substituted dihydropyranones in good to excellent yields with excellent diastereo-… Click to show full abstract

An N-heterocyclic carbene (NHC)-catalyzed asymmetric [4+2] annulation of ( E )-2-benzoyl-3-phenylacrylonitriles with α-chloroaldehydes has been developed. The protocol leads to 5-cyano-substituted dihydropyranones in good to excellent yields with excellent diastereo- and enantioselectivities (up to 93% yield, >20:1 d.r. and 99% ee).

Keywords: cyano substituted; catalyzed activation; carbene catalyzed; substituted dihydropyranones; synthesis; heterocyclic carbene

Journal Title: Synthesis
Year Published: 2017

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