Towards the Syntheses of α-Trifluoromethylated Oxygenated Heterocycles and Their Precursors

Steven Harthong; Thierry Billard; Bernard R. Langlois

doi:10.1055/s-2005-872076

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Towards the Syntheses of α-Trifluoromethylated Oxygenated Heterocycles and Their Precursors

Steven Harthong, Thierry Billard*, Bernard R. Langlois
Laboratoire SERCOF (UMR CNRS 5181), Université Claude Bernard-Lyon 1, Bât. Chevreul, 43 Bd du 11 novembre 1918, 69622 Villeurbanne, France
Fax: +33(4)72431323; e-Mail: billard@univ-lyon1.fr;

Abstract

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Abstract

The possibilities of synthesizing various α-trifluoromethylated oxygenated heterocycles, starting from trifluoroacetaldehyde methyl hemiacetal, through classic cyclization reactions, have been demonstrated. In this way, six-membered cyclic compounds, δ-lactones and also macrolactones, bearing a CF₃ group in a position α to the oxygen could be easily obtained through a RCM reaction. Bicyclic compounds could be also synthesized by an intramolecular Pauson-Khand reaction.

Key words

fluorine - metathesis - cyclizations - oxygenated heterocycles - trifluoroacetaldehyde

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