title: Mechanistic Insights into the Factors Determining Exo-Endo Selectivity in the Lewis Acid-Catalyzed Diels-Alder Reaction of 1,3-Dienes with 2-Cycloalkenones.
abstract: We adduce evidence that the asynchronous, Lewis acid-catalyzed Diels-Alder reaction of 2-cycloalkenones with nonsimple alpha,beta-enones can proceed via transition states in which the 1,3-diene subunit is skewed, i.e., nonplanar, with profound effects on the ratio of exo and endo addition products.
authors.affiliation: Department of Chemistry and Chemical Biology Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138.
authors.initials: M
authors.lastname: Ge
authors.initials: BM
authors.lastname: Stoltz
authors.initials: EJ
authors.lastname: Corey