title: SmI2-mediated coupling of nitrones and tert-butanesulfinyl imines with allenoates: synthesis of β-methylenyl-γ-lactams and tetramic acids.
abstract: Nitrones and tert-butanesulfinyl imines undergo conjugate addition to alkyl allenoates under SmI(2)-mediated reductive coupling conditions to produce novel β-methylenyl-substituted γ-amino esters. The latter were readily transformed into the corresponding β-methylenyl-γ-lactams by simple zinc reduction (N-hydroxy amines) or by acid hydrolysis (sulfinamides). The diastereoselective preparation of various β-methylenyl-γ-lactams offers a route to tetramic acids, the key structural features of an important class of bioactive natural products.
authors.affiliation: Département de Chimie Moléculaire (SERCO) UMR 5250, ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France.
authors.forename: Chu-Pei
authors.initials: CP
authors.lastname: Xu
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
authors.forename: Sandrine
authors.initials: S
authors.lastname: Py
mesh_terms: D004952:Esters; D007097:Imines / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004952:Esters; D007097:Imines; D007454:Iodides; D009589:Nitrogen Oxides; D011760:Pyrrolidinones; D047090:beta-Lactams; C015388:nitrones; D012493:Samarium; C009435:tetramic acid; D015032:Zinc; C409809:samarium diiodide