title: Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers.
abstract: [reaction: see text] The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0 degrees C resulting in complete conversion to the corresponding primary amine in up to 99% ee.
authors.affiliation: Department of Chemistry, University of Puerto Rico-Humacao, CUH Station, Humacao, Puerto Rico 00791.
authors.forename: Xiaogen
authors.initials: X
authors.lastname: Huang
authors.forename: Margarita
authors.initials: M
authors.lastname: Ortiz-Marciales
authors.forename: Kun
authors.initials: K
authors.lastname: Huang
authors.forename: Viatcheslav
authors.initials: V
authors.lastname: Stepanenko
authors.forename: Francisco G
authors.initials: FG
authors.lastname: Merced
authors.forename: Angel M
authors.initials: AM
authors.lastname: Ayala
authors.forename: Wildeliz
authors.initials: W
authors.lastname: Correa
authors.forename: Melvin De
authors.initials: MD
authors.lastname: Jesús
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000605:Amino Alcohols; D001880:Boranes; D001881:Borates; D004987:Ethers; D010091:Oximes; D013141:Spiro Compounds