✦ LIBER ✦

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

✍ Scribed by Sarah Gibson; Hollie K. Jacobs; Aravamudan S. Gopalan

Book ID: 104098764
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 886 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.12.062

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✦ Synopsis

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.

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