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Issue 4, 2013
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Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals

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Abstract

The scope of the NHC-redox amidation has been expanded to include a variety of α,β-unsaturated aldehydes, including α-fluoro α,β-unsaturated aldehydes which give rise to enantioenriched α-fluoroamides in good to excellent yield and enantioselectivity (up to 97% ee). Enantioenriched amines may be elaborated to either diastereomer of the product in high diastereoselectivity (up to 99 : 1). Functionalization of the amide products to amines and fluorohydrins is also demonstrated with retention of enantioenrichment at the fluorine stereocenter.

Graphical abstract: Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals

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Publication details

The article was received on 13 Dec 2012, accepted on 28 Jan 2013 and first published on 13 Feb 2013


Article type: Edge Article
DOI: 10.1039/C3SC00089C
Citation: Chem. Sci., 2013,4, 1674-1679
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    Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals

    P. Wheeler, H. U. Vora and T. Rovis, Chem. Sci., 2013, 4, 1674
    DOI: 10.1039/C3SC00089C

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