title: Bifunctional guanidine via an amino amide skeleton for asymmetric Michael reactions of beta-ketoesters with nitroolefins: a concise synthesis of bicyclic beta-amino acids.
abstract: Two activations are better than one: The chiral bifunctional guanidine 1, which features an amino amide backbone, catalyzes the asymmetric Michael addition of a range of substrates and gives products with excellent stereoselectivities. The method also allows the efficient synthesis of optically pure beta-amino acid esters. Both the guanidine group and the NH proton of the amide were important for the dual activation.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
authors.forename: Zhipeng
authors.initials: Z
authors.lastname: Yu
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Lin
authors.initials: L
authors.lastname: Zhou
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D019791:Guanidine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000577:Amides; D000598:Amino Acids, Cyclic; D001643:Bridged Bicyclo Compounds; D004952:Esters; D019791:Guanidine