Convergent access to mono-fluoroalkene-based peptidomimetics

Abstract

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...

Horner–Wadsworth–Emmons reaction as an excellent tool in the synthesis of fluoro-containing biologically important compounds

“…For this purpose, sulfone 9 was reacted with aldehydes 173 under LiCl and NEt 3 in THF. 117 Fluorovinylsulfone compounds 174 were synthesized in the form of Z / E isomers (ratio from 42 : 58 to 99 : 1). In the case of derivatives containing alanine, serine, and lysine in their structure, good to very good yields were observed, but only moderate Z / E selectivity.…”

Julia‐Kocienski Olefination in the Synthesis of Trisubstituted Alkenes: Recent Progress

“…Enriching the variety of the above described α ‐amino‐monofluoroalkenes, the group of Pfund and Lequeux [73] described a convergent and selective preparation of Z ‐monofluoroalkene‐based dipeptide isosteres from functionalized fluorosulfones using the Julia‐Kocienski olefination (Scheme 33). The reactivity of sulfones 177 was initially evaluated in a model reaction with benzaldehyde or p ‐bromobenzaldehyde where it was found that phthalimido‐sulfone 177 a gave the best results regarding yield and Z ‐selectivity.…”