title: Nucleophilic ring-opening of epoxide and aziridine acetates for the stereodivergent synthesis of β-hydroxy and β-amino γ-lactams.
abstract: A highly regio- and stereoselective synthesis of novel β,γ-disubstituted γ-lactams with either an anti or syn relative configuration was developed from readily available epoxide and aziridine acetates. The key steps include the regio- and diastereocontrolled nucleophilic ring-opening of these three-membered heterocycles followed by mild reductive cyclization of the γ-azido ester intermediate. The method was also extended to an asymmetric synthesis of (4R,5S)-4-hydroxy-5-phenylpyrrolidin-2-one from a chiral epoxide acetate. The main features of this versatile synthesis of functionalized γ-lactams include the involvement of inexpensive reagents and mild conditions together with high chemical efficiency.
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil.
authors.forename: Tula B
authors.initials: TB
authors.lastname: Bisol
authors.forename: Adailton J
authors.initials: AJ
authors.lastname: Bortoluzzi
authors.forename: Marcus M
authors.initials: MM
authors.lastname: Sá
mesh_terms: D000085:Acetates / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C558058:(4R,5S)-4-hydroxy-5-phenylpyrrolidin-2-one; D000085:Acetates; D001388:Aziridines; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D011760:Pyrrolidinones; D047090:beta-Lactams; C033132:aziridine