title: Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds.
abstract: The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Sasano
authors.forename: Shota
authors.initials: S
authors.lastname: Nagasawa
authors.forename: Mai
authors.initials: M
authors.lastname: Yamazaki
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Shibuya
authors.forename: Jaiwook
authors.initials: J
authors.lastname: Park
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009930:Organic Chemicals; D010084:Oxidation-Reduction
chemical_list: D000605:Amino Alcohols; D009930:Organic Chemicals
keywords: amino alcohol; chemoselectivity; copper; oxidation; radical chemistry