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Asymmetric NHC-catalyzed synthesis of ?-fluoroamides from readily accessible ?-fluoroenals.

ABSTRACT: The scope of the NHC-redox amidation has been expanded to include a variety of ?,?-unsaturated aldehydes, including ?-fluoro ?,?-unsaturated aldehydes which give rise to enantioenriched ?-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.

SUBMITTER: Wheeler P

PROVIDER: S-EPMC4205762 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.

Wheeler Philip P Vora Harit U HU Rovis Tomislav T

Chemical science 20130401 4

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 enan ...[more]

PMID: 25346841

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