On the Bis‐Heteronucleophilic Michael Addition to Divinyl Sulfone: A New Efficient Access to Macrocycles by Marie‐Laure Teyssot, Martine Fayolle, Christian Philouze and Claude Dupuy

Abstract

This is a comment on the paper by Dupuy et al. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

A General Route to Mono- and Disubstituted Divinyl Sulfones: Acyclic Michael Acceptors for the Synthesis of Polyfunctionalized Cyclic Sulfones

“…Divinyl sulfone (DVS) or 1,1′-sulfonylbisethene ( 1 , Scheme ) is a unique molecule having diverse applications in chemistry , and biology . Conjugate addition of carbon nucleophiles and heteronucleophilic addition of primary amines, thiols, selenium, tellurium, and phosphanes to the two vinyl groups of 1 constitute a class of efficient and synthetically useful reactions for the generation of cyclic compounds represented by the general structure 2 (Scheme ). − Compound 1 has also been used in the preparation of macrocycles , and polymeric compounds . DVS 1 is shown to be a component of the Stetter reaction in the synthesis of 1,4-diketo derivatives …”