title: Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling.
abstract: Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.
authors.forename: Christopher H
authors.initials: CH
authors.lastname: Schuster
authors.forename: John R
authors.initials: JR
authors.lastname: Coombs
authors.forename: Zachary A
authors.initials: ZA
authors.lastname: Kasun
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D011083:Polycyclic Compounds; D010165:Palladium
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