Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes

Romain Laporte (1) , Anais Prunier (1) , Emmanuel Pfund (1) , Vincent Roy (2) , Luigi Agrofoglio (2) , Thierry Lequeux (1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 ICOA - Institut de Chimie Organique et Analytique

Access to fluoroalkylidene-oxetanes and-azetidines was realized from 3-oxetanone, 3-azetidinone, and fluorosulfones through the Julia-Kocienski reaction. This approach allows the preparation of new precursors of fluorinated four-membered rings that contain a nucleic base, an ester or aryl sulfone function, and a pyrrolidine ring. Benzothiazolyl-sulfonemediated aza-Michael addition reaction of nitrogen nucleophiles enables access to 3,3-disubstituted oxetanes.

Domaines: Chimie organique

Romain Laporte, Anais Prunier, Emmanuel Pfund, Vincent Roy, Luigi Agrofoglio, et al.. Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes. European Journal of Organic Chemistry, 2015, 2015 (14), pp.3121-3128. ⟨10.1002/ejoc.201500172⟩. ⟨hal-02348052⟩