Organic Letters [SOPHY]

Abstract:

The first synthesis of gem-difluorinated ene–ynamides is presented via deprotonation of trifluoromethylated N-allenamides and δ extrusion of fluorine. These highly reactive building blocks, owing to their dual functional groups, offer a unique entry to difluorinated dienes and to stereodefined, monofluoro-substituted dienes. Stereoselective addition to the ynamide moiety led to difluorinated dienes. A stereocontrolled domino δ elimination reaction followed by an addition/elimination sequence from trifluoromethylated N-allenamides provided exclusively stereodefined monofluorinated ene–ynamides.

Reference :

Maxime Hourtoule and Laurence Miesch

Regio- and Stereoselective Addition to gem-Difluorinated Ene–Ynamides: Access to Stereodefined Fluorinated Dienes

Organic Letters, Articles ASAP (Letter), Publication Date (Web):May 19, 2022 - DOI: 10.1021/acs.orglett.2c01593

Contact:

Laurence Miesch, équipe SOPhy, Institut de Chimie (UMR 7177).