title: Rhodium-catalyzed ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with arylboronic acids.
abstract: Rhodium-catalyzed ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with arylboronic acids were investigated. The use of [RhCl(COD)](2), (+/-)-BINAP, and NaHCO(3) in MeOH at 60 degrees C was found to be the optimized conditions for the ring-opening reactions to give the 1,2-ring-opened products. Various arylboronic acids were examined, and low to moderate yields were obtained and stereoselectivities (trans/cis) from 50:50 to 100:0 were observed.
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
authors.forename: Ben P
authors.initials: BP
authors.lastname: Machin
authors.forename: Melissa
authors.initials: M
authors.lastname: Ballantine
authors.forename: Jérémie
authors.initials: J
authors.lastname: Mandel
authors.forename: Nicolas
authors.initials: N
authors.lastname: Blanchard
authors.forename: William
authors.initials: W
authors.lastname: Tam
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C540994:3-aza-2-oxabicyclo(2.2.1)hept-5-ene; D001897:Boronic Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004952:Esters; D009942:Organometallic Compounds; D012238:Rhodium