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Updated: Apr 21, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals
Philip Wheeler1, Harit U Vora1, Tomislav Rovis1
1Department of Chemistry, Colorado State University, Fort Collins, CO, U. S. A. 80523 Tel: (970) 491-
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.
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