title: Organocatalytic one-pot oxidative cleavage of terminal diols to dehomologated carboxylic acids.
abstract: The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO(2) caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan. m-shibu@ps.nagoya-u.ac.jp
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Shibuya
authors.forename: Ryūsuke
authors.initials: R
authors.lastname: Doi
authors.forename: Takuro
authors.initials: T
authors.lastname: Shibuta
authors.forename: Shun-ichiro
authors.initials: S
authors.lastname: Uesugi
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D005609:Free Radicals / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D002264:Carboxylic Acids; D005609:Free Radicals; D009589:Nitrogen Oxides; C039900:nitroxyl