title: A C-F Bond Directed Diels-Alder Reaction.
abstract: We demonstrate a C-F bond driven Diels-Alder reaction of a fluorinated dienophile and a borole that shows remarkable diastereoselectivity. The product's structure was confirmed by X-ray crystallography, revealing an unusual conformation featuring a hypercoordinate boron. Calculations suggest that a B···F interaction instigates the reaction chemistry, the magnitude of which is maximized in the transition state-in essence, the B···F distance "yo-yos" from long to short in the transition state and back again to long in the product.
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Mark D
authors.initials: MD
authors.lastname: Struble
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Liangyu
authors.initials: L
authors.lastname: Guan
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Maxime A
authors.initials: MA
authors.lastname: Siegler
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka