title: Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols.
abstract: The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.
authors.affiliation: †Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama 6-3, Sendai 980-8578, Japan.
authors.forename: Ryusuke
authors.initials: R
authors.lastname: Doi
authors.affiliation: ‡Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Shibuya
authors.affiliation: ‡Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors.forename: Tsukasa
authors.initials: T
authors.lastname: Murayama
authors.affiliation: ‡Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Yamamoto
authors.affiliation: †Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama 6-3, Sendai 980-8578, Japan.
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000438:Alcohols; D000447:Aldehydes; D002264:Carboxylic Acids; D005609:Free Radicals; D009589:Nitrogen Oxides; C039900:nitroxyl; D000218:Adamantane