Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones. -Reduction of ester (I) followed by S-oxidation and dehydration results in formation of the vinylsulfone (IV). The latter smoothly undergoes addition with amines, amino acid esters, and imidazole to afford the title compounds. It also reacts with alkyl iodides giving sulfones of type (XIV). They are useful synthons which allow formation of diverse fluoroolefins.-(CALATA, C.; PFUND, E.; LEQUEUX*, T.; J. Org. Chem. 74 (2009)
Aza-Michael Access to Fluoroalkylidene Analogues of Biomolecules. -A direct access for the preparation of fluoroallylamines via aza-Michael reaction followed by a modified Julia reaction is presented. This method also allows the synthesis of fluorovinylic acyclic nucleoside (XIV), which exhibits anti-cancer properties, as well as the synthesis of the DPP-II inhibitor (XVIII). -(PRUNIER, A.; CALATA, C.; LEGROS, J.; MADDALUNO, J.; PFUND, E.; LEQUEUX*, T.; J. Org. Chem. 78 (2013) 16, 8083-8097, http://dx.
Sulfones Q 0600Scope and Limitations of the Julia-Kocienski Reaction with Fluorinated Sulfonylesters. -Various fluoroalkenes are obtained from βand δ-substituted cyclic ketones but mostly without any selectivity. The reaction of (VIII) performed with DBU in ethyl acetate in the presence of a catalytic amount of water leads to the decarbethoxylated sulfone (X). The latter approach is used to prepare new fluorinated alkylsulfones via alkylation and following decarbethoxylation. -(CALATA, C.; CATEL, J.-M.; PFUND, E.; LEQUEUX*, T.; Tetrahedron 65 (2009) 20, 3967-3973; Lab. Chim. Mol. Thio-Org., CNRS, Ec. Natl. Super. Ing., Univ. Caen, F-14050 Caen, Fr.; Eng.) -Y. Steudel 37-075
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.