Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect

  • Chincholkar P
  • Puranik V
  • Deshmukh A
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Diastereoselective synthesis of spiro-β-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive d-glucose. Although, theoretically four diastereomers are possible, the reaction yielded only two diastereomers stereoselectively in good to moderate yields. The stereochemical outcome of the reaction was in accordance with the torquoelectronic model. © 2007 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Imines
  • Ketenes
  • Spiro-β-lactams
  • Staudinger reaction
  • Stereoselective synthesis

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  • P. M. Chincholkar

  • Vedavati G. Puranik

  • A. R.A.S. Deshmukh

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