title: Rhodium-catalyzed synthesis of 3-hydroxy-beta-lactams via oxonium ylide generation: three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols.
abstract: 3-Substituted-3-hydroxy-beta-lactams, with two new adjacent stereogenic centers, have been prepared in a single step by a rhodium-catalyzed, three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols. Good to moderate stereoselectivity was obtained depending on the alcohol used. The stereochemistry of the new centers has been undoubtedly assigned by single crystal X-ray diffraction.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain. alcaideb@quim.ucm.es
authors.forename: Benito
authors.initials: B
authors.lastname: Alcaide
authors.forename: Pedro
authors.initials: P
authors.lastname: Almendros
authors.forename: Cristina
authors.initials: C
authors.lastname: Aragoncillo
authors.forename: Ricardo
authors.initials: R
authors.lastname: Callejo
authors.forename: M Pilar
authors.initials: MP
authors.lastname: Ruiz
authors.forename: M Rosario
authors.initials: MR
authors.lastname: Torres
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D012238:Rhodium / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000438:Alcohols; D001384:Azetidines; D003979:Diazonium Compounds; D007769:Lactams; D012238:Rhodium; C032111:diazoacetic ester