title: Direct asymmetric N-specific reaction of nitrosobenzene with aldehydes catalyzed by a chiral primary amine-based organocatalyst.
abstract: Nitroso compounds have two reactive nitrogen and oxygen atoms. It is interesting and important to perform a nitrogen or oxygen selective reaction with interesting substrates. These atom specific reactions are crucial to specifically synthesis of specific compounds. An enantioselective N-specific reaction of nitrosobenzene with unmodified aldehydes was successfully achieved catalyzed first by a variety of primary amine-based organocatalysts with higher yield and enantioselectivity. The bulkier substituted groups of the organocatalyst and two hydrogen bonds from the organocatalyst and the oxygen atom of nitrosobenzene make the reaction preferentially N-specific and predominantly afford R products.
authors.affiliation: Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China.
authors.forename: Long
authors.initials: L
authors.lastname: Qin
authors.forename: Lei
authors.initials: L
authors.lastname: Li
authors.forename: Lei
authors.initials: L
authors.lastname: Yi
authors.forename: Chao-Shan
authors.initials: CS
authors.lastname: Da
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Zhou
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D009584:Nitrogen / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000447:Aldehydes; D000588:Amines; D009603:Nitroso Compounds; D009584:Nitrogen; C012456:nitrosobenzene