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Updated: Jul 2, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Asymmetric Fluorocyclization of Difluoroalkenes with Concomitant Formation of a Trifluoromethyl Group
Chino Igarashi1, Tomoya Mayumi1, Hiromichi Egami1
1School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Abstract:
Asymmetric electrophilic fluorination of difluoroalkenes remains undeveloped because of the poor reactivity of difluoroalkenes with electrophiles. However, such reactions, if feasible, are expected to be useful for the synthesis of chiral heterocyclic compounds with a trifluoromethyl group at the stereogenic center. In this Letter, we disclose the first example of asymmetric fluoroamide cyclization of difluoroalkenes using our dianionic phase-transfer catalyst. This reaction provides unique chiral trifluoromethylated oxazoline derivatives at a synthetically useful level.
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