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Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst

Authors


  • We thank NIGMS for generous support of this research (GM 36700 to K.N.H. and GM 72586 to T.R.). T.R. thanks Amgen and Roche for unrestricted support. E.L.N. is grateful to the National Institutes of Health Chemistry-Biology Interface Training Program Grant (T32M008496). K.N.H. is grateful to the National Science Foundation (CHE-0548209) for financial support, to the UCLA Academic Technology Services (ATS) Hoffman2 and IDRE clusters for computational resources, and for the TeraGrid resources provided by NCSA (CHE-0400414).

Abstract

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Fluorine helps: A fluorinated triazolium salt precatalyst has been developed that efficiently promotes the asymmetric intermolecular Stetter reaction of enolizable aldehydes and nitrostyrenes (see scheme). Trans fluorination of the catalyst architecture results in unparalleled reactivity and enantioselectivity in the desired transformation. A DFT study provides evidence of an electrostatic interaction as the source of the increased enantio-induction.

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