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The convergent and selective preparation of (Z)-monofluoroalkene-based dipeptide isosteres from functionalized fluorosulfones as a cornerstone is described. In this approach, the N-terminal amino group is introduced by a conjugate addition reaction of phthalimide onto fluorinated vinylsulfones containing α-amino-acid side chains while the C-terminal motif is linked to the fluorovinylic peptide bond mimic via the Julia–Kocienski reaction between fluorosulfones and substituted aldehydes bearing α-amino-acid side chains.

Graphical abstract: Convergent access to mono-fluoroalkene-based peptidomimetics

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