Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones

Abstract

Due to the importance of allylamines in organic synthesis, the synthesis of reagents as potent precursors of aminofluoroolefins is reported from functionalized benzothiazolylsulfones. The key intermediate, a fluorovinyl sulfone, was prepared and functionalized by addition of aliphatic, aromatic amines and amino acid alkyl esters through an aza-Michael addition reaction.

Synthesis of Fluorine‐Containing 3,3‐Disubstituted Oxetanes and Alkylidene Oxetanes

“…The use of substituted ketones is rare because competitive reactions occur with substituted ketones. [32,33] With a different route to π-deficient heterocyclic fluorosulfones on hand, [32][33][34][35][36] investigation and prep-the Julia-Kocienski reaction performed with sulfones 1 and 2 afforded corresponding oxetanes 5a-5c in 50-94 % yields. With sulfone 3 the reaction reached completion after 3 h at 20°C, and crude 5d ( 19 F NMR: -118.9 ppm, triplet of quintet, 18.4 and 3.4 Hz) was unstable.…”

Synthesis of Fluorinated exo‐Glycals through Modified Julia Olefination

“…Fluoroalkyl sulfones were prepared according to a literature procedure, [15] and their addition to lactones was tested to prepare exo-glycals. The reaction was first performed with 2,3,4,6-tetra-O-benzyl-d-gluconolactone and 2-benzothiazolyl fluoromethyl sulfone (Scheme 1).…”

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

“…In 2011, Lequeux and co-workers used rather the Julia–Kocienski olefination to access Phth-Gly-ψ[CF=CH]-Gly 9 , from benzothiazolyl fluoroaminosulfones ( Scheme 2 ) [ 24 – 25 ]. The Julia–Kocienski olefination of 3-alkoxypropanal 7 with phthalimido sulfone 6 afforded the corresponding monofluoroalkene 8 as a ( Z ):( E ) mixture (54:46).…”