title: Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives.
abstract: A new, facile, and highly stereoselective protocol toward alpha,beta-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples. [reaction: see text]
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Dianjun
authors.initials: D
authors.lastname: Chen
authors.forename: Li
authors.initials: L
authors.lastname: Guo
authors.forename: Junying
authors.initials: J
authors.lastname: Liu
authors.forename: Sameer
authors.initials: S
authors.lastname: Kirtane
authors.forename: John F
authors.initials: JF
authors.lastname: Cannon
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D000596:Amino Acids / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones