title: Functionalized chromans and isochromans via a diastereoselective Pd(0)-catalyzed carboiodination.
abstract: A diastereoselective approach to isochromans and chromans via Pd(0)-catalyzed carboiodination is reported. The transformations using this methodology display excellent yields and diastereoselectivities as well as broad functional group compatibility. The selectivity observed in these cyclizations, forming isochroman or chroman targets, is postulated to originate from the minimization of A(1,2) strain and axial-axial interactions, respectively. This method has also been used to highlight the concept of reversible oxidative addition to carbon-iodine bonds in polyiodinated substrates.
authors.affiliation: Department of Chemistry, Davenport Chemical Laboratories, 80 St. George Street, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
authors.forename: David A
authors.initials: DA
authors.lastname: Petrone
authors.forename: Hasnain A
authors.initials: HA
authors.lastname: Malik
authors.forename: Antonin
authors.initials: A
authors.lastname: Clemenceau
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002839:Chromans; D006847:Hydrocarbons, Iodinated; D010165:Palladium