title: Studies of intramolecular Diels-Alder reactions of nitroalkenes for the stereocontrolled synthesis of trans-decalin ring systems.
abstract: Studies of thermal IMDA cyclizations of (1E,7E)-1-nitro-deca-1,7,9-trienes and (1E,3Z,7E)-1-nitro-deca-1,3,7,9-tetraenes have been examined. Reactions of these nitroalkenes proceed via transition states featuring characteristics of asymmetric stretch asynchronicity and result in stereoselective formation of trans-fused decalin products. A substantial rate acceleration is observed for IMDA cyclizations exemplified by triene 14 due to steric repulsions of substituents in the tethering chain which promote facile stereocontrolled formation of trans-fused 26.
authors.affiliation: Department of Chemistry, Indiana University, Bloomington, IN 47405, United States.
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.forename: J Cullen
authors.initials: JC
authors.lastname: Klein
authors.forename: Nicholas S C
authors.initials: NS
authors.lastname: Chow