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

  • Chincholkar P
  • Puranik V
  • Deshmukh A
  • 5

    Readers

    Mendeley users who have this article in their library.
  • 15

    Citations

    Citations of this article.

Abstract

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

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Authors

  • P. M. Chincholkar

  • Vedavati G. Puranik

  • A. R.A.S. Deshmukh

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free