Synthesis of beta-lactams from diazoketones and imines: the use of microwave irradiation

Org Lett. 2001 Jun 14;3(12):1849-51. doi: 10.1021/ol015891+.

Abstract

[see reaction]. The transformation of diazoketones derived from alpha-amino acids to ketenes that, in turn, react further with imines to afford beta-lactams, can be realized not only by utilizing photochemical reaction conditions but also under the action of microwave irradiation. Under the latter reaction conditions 4-alkenyl-substituted beta-lactams derived from amino acids, substrates that were not previously accessible, have been prepared. beta-Lactams possessing a trans-substitution pattern at the ring were obtained exclusively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry
  • Imines / chemistry*
  • Ketones / chemistry*
  • Microwaves*
  • beta-Lactams / chemical synthesis*
  • beta-Lactams / chemistry

Substances

  • Azo Compounds
  • Imines
  • Ketones
  • beta-Lactams