title: Cu(I)-catalyzed synthesis of dihydropyrimidin-4-ones toward the preparation of β- and β3-amino acid analogues.
abstract: A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80-95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety of reactive nucleophiles, the obtained substituted dihydropyrimidin-4-ones were elegantly transformed into the corresponding β- and β(3)-amino acid analogues.
authors.affiliation: Department of Chemistry, National Sun Yat-sen University , Kaohsiung 804, Taiwan.
authors.forename: Basker
authors.initials: B
authors.lastname: Rajagopal
authors.forename: Ying-Yu
authors.initials: YY
authors.lastname: Chen
authors.forename: Chun-Chi
authors.initials: CC
authors.lastname: Chen
authors.forename: Xuan-Yu
authors.initials: XY
authors.lastname: Liu
authors.forename: Huei-Ren
authors.initials: HR
authors.lastname: Wang
authors.forename: Po-Chiao
authors.initials: PC
authors.lastname: Lin
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D011744:Pyrimidinones; D003300:Copper; D010293:Pargyline