title: Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of 2-allyloxypyridines and related heterocycles.
abstract: Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of (E)- and (Z)-allyloxy substituted N-heterocycles generates N-allyl N-heterocyclic amides in good yields and high enantioselectivities (up to 96% ee). The chiral palladacycle COP-Cl (5 mol %) is used as a catalyst with silver(I) trifluoroacetate (10 mol %) at 35-45 degrees C. Examples of heterocycles synthesized include 2-pyridones, quinolin-2(1H)-ones, and isoquinolin-1(2H)-ones.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Rodrigues
authors.forename: Ernest E
authors.initials: EE
authors.lastname: Lee
authors.forename: Robert A
authors.initials: RA
authors.lastname: Batey
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D011725:Pyridines; D010165:Palladium