Synthesis 2005(13): 2253-2263  
DOI: 10.1055/s-2005-872076
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 21 June 2005
Publication Date:
20 July 2005 (eFirst)

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.