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-mem-
The synthesis of fluoroaminosulfones derived from piperidine and nucleic bases followed by the study of their chemical behavior in the modified Julia reaction are described. The resulting aminosulfones open a straightforward access to a series of new fluorinated biomolecules including a potent DPP-II inhibitor and acyclonucleoside analogues as potential enzyme inhibitors.
The convergent and selective preparation of (Z)-monofluoroalkene-based dipeptide isosteres from functionalized fluorosulfones as cornerstone is described. In this approach, the N-terminal amino group is introduced by a conjugate addition reaction...
The introduction of fluoroalkylidenes onto 3‐oxetanone, 3‐azetidinone, and cyclobutanone rings is achieved through base mediated reaction with various sulfones.
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.
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