1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis: Stereoselective Homo- and Hetero-Diels-Alder Reactions

Palladium-catalysed coupling of a vinylstannane or vinyl boronic acids with 5-iodo-1,4-bis(tosyl)-1,2,3,4-tetrahydro pyridines yields 1,3-dienes. These participate in homo- and hetero-Diels-Alder reactions with unsaturated carbonyl compounds and with nitroso species generated in situ to give novel bicyclic compounds in a highly stereoselective fashion.