title: Aniline mediated oxidative C-C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(D)-amino acid derivatives.
abstract: A metal-free and 4-methyl aniline mediated method for the oxidative C-C bond cleavage has been developed. The reaction proceeds in air using molecular oxygen as the oxidant, affording one-carbon shortened esters in moderate to good yields within a short time. Moreover, it provides a model reaction for the highly enantioselective synthesis of (D)-serine esters by combining with a l-proline catalyzed Mannich reaction.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, PR China.
authors.forename: Bin
authors.initials: B
authors.lastname: Hu
authors.forename: Yunfeng
authors.initials: Y
authors.lastname: Li
authors.forename: Zhongjun
authors.initials: Z
authors.lastname: Li
authors.forename: Xiangbao
authors.initials: X
authors.lastname: Meng
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D000814:Aniline Compounds; D012694:Serine; D010100:Oxygen; C023650:aniline