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

TETRAHEDRON LETTERS

卷:52

Article

Gibson, Sarah¹  Jacobs, Hollie K.¹  Gopalan, Aravamudan S.¹ 

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

关键词: Lactam;    Chiral oxazolidinone;    Intramolecular cyclization;    Levetiracetam;    Asymmetric synthesis;    Carbanions;   

DOI  :  10.1016/j.tetlet.2010.12.062

来源: Elsevier

【 摘 要 】

The intramolecular cyclizations of oxazolidinones with carbanions adjacent to sulfones, sulfoxides, and phosphonates proceed in high yields to obtain functionalized gamma and delta 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. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

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