title: Control of selectivity in the generation and reactions of oxonium ylides.
abstract: Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Deana M
authors.initials: DM
authors.lastname: Jaber
authors.forename: Ryan N
authors.initials: RN
authors.lastname: Burgin
authors.forename: Matthew
authors.initials: M
authors.lastname: Hepler
authors.forename: Peter
authors.initials: P
authors.lastname: Zavalij
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D000090:Acetoacetates / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D008958:Models, Molecular; D011753:Pyrones / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000090:Acetoacetates; D001643:Bridged Bicyclo Compounds; D011753:Pyrones; C016635:acetoacetic acid; D012238:Rhodium