title: Asymmetry by electrophilic rearrangement of symmetric 2-pyridone photodimers.
abstract: [reaction: see text] Halogenation of achiral trans-2-pyridone photodimers results in 1,3-migration of an amide nitrogen and formation of a chiral structure with six stereogenic centers and well-differentiated functionality. The reactivity of this product toward nucleophiles, including the allylic halide, is dominated by participation by the amide nitrogen.
authors.affiliation: Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794, USA.
authors.forename: Yeon-Hee
authors.initials: YH
authors.lastname: Lim
authors.forename: Tindy
authors.initials: T
authors.lastname: Li
authors.forename: Peiling
authors.initials: P
authors.lastname: Chen
authors.forename: Patrick
authors.initials: P
authors.lastname: Schreiber
authors.forename: Larissa
authors.initials: L
authors.lastname: Kuznetsova
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Joseph W
authors.initials: JW
authors.lastname: Lauher
authors.forename: Scott McN
authors.initials: SM
authors.lastname: Sieburth
mesh_terms: D000577:Amides / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D006843:Hydrocarbons, Chlorinated; D011728:Pyridones