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Synlett 1992; 1992(4): 313-314
DOI: 10.1055/s-1992-21996
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Kinetic Resolution of a β-Lactam Using Homochiral Lithium Amide Chemistry

Peter Coggins* , Nigel S. Simpkins
  • *Department of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, England
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Publication Date:
08 March 2002 (online)

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A racemic β-lactam [1-tert-butyldimethylsilyl-4-phenylthioazetidin-2-one (3)] was subjected to kinetic resolution using a homochiral lithium amide base [lithium (R,R)-bis(1-phenylethyl)amide (2)]. Reaction of the so-formed non-racemic carbanion with chlorotrimethylsilane gives an α-silylated β-lactam product 6 in up to 72% enantiomeric excess, whilst reaction with acetaldehyde allows access to α-acetyl β-lactam 7, an intermediate in the synthesis of thienamycin, in similar optical purity.