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

The intramolecular cyclizations of chiral oxazolidinones with carbanions adjacent to sulfones, sulfoxides, and phosphonates proceeds in excellent yields to obtain functionalized γ and δ lactams. The lactams from this study are useful synthetic intermediates, as demonstrated by the synthesis of a pre...

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Bibliographic Details
Published in:Tetrahedron letters 2011-02, Vol.52 (8), p.887-890
Main Authors: Gibson, Sarah, Jacobs, Hollie K., Gopalan, Aravamudan S.
Format: Article
Language:English
Subjects:
Amides
Amino acids
Asymmetric synthesis
Carbanions
Chiral oxazolidinone
Drugs
Intramolecular cyclization
Lactam
Levetiracetam
Phosphonates
Precursors
Sulfones
Synthesis (chemistry)
Tetrahedrons
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Summary:The intramolecular cyclizations of chiral oxazolidinones with carbanions adjacent to sulfones, sulfoxides, and phosphonates proceeds in excellent yields to obtain functionalized γ and δ lactams. The lactams from this study are useful synthetic intermediates, as demonstrated by the synthesis of a precursor for levetiracetam, an antiepileptic drug. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.12.062