title: Effect of counterion structure on rates and diastereoselectivities in α,β-unsaturated iminium-ion Diels-Alder reactions.
abstract: The use of cyclic α,β-unsaturated iminium-ion dienophiles is documented in two highly diastereoselective Diels-Alder (DA) reactions. The dienophilic counterion was found to have a significant effect on reactivity.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: David
authors.initials: D
authors.lastname: Marcoux
authors.forename: Pascal
authors.initials: P
authors.lastname: Bindschädler
authors.forename: Alexander W H
authors.initials: AW
authors.lastname: Speed
authors.forename: Anna
authors.initials: A
authors.lastname: Chiu
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Pero
authors.forename: George A
authors.initials: GA
authors.lastname: Borg
authors.forename: David A
authors.initials: DA
authors.lastname: Evans
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000470:Alkaloids; D001372:Aza Compounds; D007097:Imines; D007783:Lactones; D013141:Spiro Compounds; C447983:pinnatoxin A; C561221:spiro-prorocentrimine