Tetrahedron letters

Chiral oxazolidinones as electrophiles: intramolecular cyclization reactions with carbanions and preparation of functionalized lactams

S Gibson, HK Jacobs, AS Gopalan

Index: Gibson, Sarah; Jacobs, Hollie K.; Gopalan, Aravamudan S. Tetrahedron Letters, 2011 , vol. 52, # 8 p. 887 - 890

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Citation Number: 4

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.