S. Benetti, C. D. Risi, P. Marchetti
2002
Citations
0
Influential Citations
6
Citations
Journal
Synthesis
Abstract
Wittig reaction of 4-((4-methylphenyl)sulfonyl)-1- (triphenylphosphoranylidene)butan-2-one (1) with N-protected - amino aldehydes furnished N-protected -amino- , -unsaturated keto sulfones which have been conveniently utilized as precursors of both aromatic and non-aromatic 2,5-disubstituted five-mem- bered heterocyclic compounds. While 2,5-disubstituted pyrroles are efficiently formed by cyclodehydration of the starting materials, 2,5-disubstituted pyrrolidines and pyrrolenines could be obtained by prior reduction of the conjugated double bond followed by acid- or base-mediated cyclization. The ready availability of the materials required for the whole sequence makes this methodology a conve- nient way to generate both aromatic and saturated 2,5-disubstituted five-membered heterocyclic compounds.