title: Ligand-controlled selectivity in the desymmetrization of meso cyclopenten-1,4-diols via rhodium(I)-catalyzed addition of arylboronic acids.
abstract: A highly enantioselective desymmetrization of meso cyclopent-2-ene-1,4-diethyl dicarbonates has been developed using a Rh-catalyzed asymmetric allylic substitution. Depending on the type of ligand used, each of two regioisomeric products can be obtained in good yield and excellent enantioselectivity. Under rhodium(I) catalysis, bisphosphine P-Phos ligands form trans-1,2-arylcyclopentenols as the major product, whereas Segphos ligands lead predominantly to trans-1,4-arylcyclopentenols.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Frederic
authors.initials: F
authors.lastname: Menard
authors.forename: David
authors.initials: D
authors.lastname: Perez
authors.forename: Daniela
authors.initials: D
authors.lastname: Sustac Roman
authors.forename: Timothy M
authors.initials: TM
authors.lastname: Chapman
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D008024:Ligands; D012238:Rhodium