151535-32-9Relevant academic research and scientific papers
Intramolecular Diels-Alder Reaction of Vinylsulfonates Derived from Hydroxyalkyl Substituted 1,3-Dienes and Oxidative Desulfurization of the Resultant Sultones
Metz, Peter,Fleischer, Michael,Froelich, Roland
, p. 711 - 732 (1995)
Vinylsulfonates prepared from hydroxyalkyl substituted cycloalka-1,3-dienes and acyclic 1,3-dienes by esterification with vinylsulfonyl chloride cycloadd to δ-sultones at temperatures ranging from 0 deg C to reflux in toluene.High diastereoselectivity is observed for substrates 2 featuring a cyclic 1,3-diene moiety, whereas a substituent R2 larger than hydrogen is necessary to achieve good to excellent levels of stereocontrol for substrates 9 possessing an acyclic 1,3-diene unit.Oxidative desulfurization of the resultant sultones via borylation and subsequent peracid treatment yields hydroxy ketones, thus establishing vinylsulfonyl chloride as a regio- and stereoselectively reacting ketene equivalent for the intramolecular Diels-Alder cycloaddition.
