title: Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes.
abstract: [reaction: see text] A rationale for regioselection in phosphine-promoted annulations of acrylates, imines, and aldehydes with allenoates has been developed using computation at the B3LYP/6-31G(d) level of theory. The computed transition states revealed that Lewis acid activation, strong hydrogen bonding (H-bonding), and minimization of unfavorable van der Waals contacts are the guiding factors responsible for regioselection. An excellent level of correlation between the calculated regioselectivities and experiment was observed.
authors.affiliation: Department of Chemistry, Brock University, St. Catharines, Ontario LS2 3A1, Canada. tdudding@brocku.ca
authors.forename: Travis
authors.initials: T
authors.lastname: Dudding
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
authors.forename: Evan
authors.initials: E
authors.lastname: Mercier