Fluorinated 2-Azetines: Synthesis, Applications, Biological Tests, and Development of a Catalytic Process
Romain Losa, Charlotte Lorton, Pascal Retailleau, Jérôme Bignon, Arnaud Voituriez
Abstract
An efficient and straightforward phosphine-promoted tandem aza-Michael addition/intramolecular Wittig reaction was developed for the synthesis of polyfunctionalized 2-azetines. After demonstrating that this transformation could be made catalytic in phosphine through in situ reduction of phosphine oxide with phenylsilane, different post-transformation steps have been demonstrated, including an original [2 + 2] photodimerization. Preliminary biological tests highlighted that these fluorinated 1,2-dihydroazete-2,3-dicarboxylates exhibited significant cytotoxicity against the human tumor cell line.
Topics & Concepts
PhosphineChemistryPhosphine oxidePhenylsilaneTandemCatalysisIntramolecular forceWittig reactionCombinatorial chemistryCytotoxicityOrganic chemistryBiochemistryMaterials scienceComposite materialIn vitroFluorine in Organic ChemistrySynthesis and Catalytic ReactionsSynthesis and Biological Evaluation