title: Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.
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.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO, U. S. A. 80523 Tel: (970) 491-
authors.forename: Philip
authors.initials: P
authors.lastname: Wheeler
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO, U. S. A. 80523 Tel: (970) 491-
authors.forename: Harit U
authors.initials: HU
authors.lastname: Vora
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO, U. S. A. 80523 Tel: (970) 491-
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis