title: Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.
abstract: A diastereoselective approach to deoxypropionate derivatives through Pd/C-catalyzed hydrogenolysis of enantioenriched ketene heterodimers is described. Catalytic hydrogenolysis of the Z-isomer of ketene heterodimers facilitates access to anti-deoxypropionate derivatives (10 examples with dr 7:1 to >20:1). Transfer of chirality from the Z-ketene heterodimer to an acid product was good to excellent in most cases (78-99% ee for 12 examples).
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Shi
authors.initials: S
authors.lastname: Chen
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Ahmad A
authors.initials: AA
authors.lastname: Ibrahim
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Mukulesh
authors.initials: M
authors.lastname: Mondal
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Magee
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Adam J
authors.initials: AJ
authors.lastname: Cruz
authors.affiliation: ‡Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, Illinois 61920-3099, United States.
authors.forename: Kraig A
authors.initials: KA
authors.lastname: Wheeler
authors.affiliation: †Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, United States.
authors.forename: Nessan J
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005030:Ethylenes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D005030:Ethylenes; D007659:Ketones; D011422:Propionates; D010165:Palladium; C008223:ketene