title: Chiral oxazolidinones as electrophiles: Intramolecular cyclization reactions with carbanions and preparation of functionalized lactams.
abstract: The intramolecular cyclizations of oxazolidinones with carbanions adjacent to sulfones, sulfoxides and phosphonates proceed in high yields to obtain functionalized γ and δ lactams. The chiral oxazolidinone precursors can be readily synthesized from commercial amino acids. The lactams from this study are useful synthetic intermediates, as demonstrated by the synthesis of a precursor for levetiracetam, an antiepileptic drug.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University Las Cruces, NM 88003-8001.
authors.forename: Sarah
authors.initials: S
authors.lastname: Gibson
authors.forename: Hollie K
authors.initials: HK
authors.lastname: Jacobs
authors.forename: Aravamudan S
authors.initials: AS
authors.lastname: Gopalan