One-pot synthesis of lactams using domino reactions: combination of Schmidt reaction with Sakurai and aldol reactions

J Org Chem. 2009 Oct 16;74(20):7618-26. doi: 10.1021/jo901843w.

Abstract

A series of domino reactions in which the intramolecular Schmidt reaction is combined with either a Sakurai reaction, an aldol reaction, or both is reported. The Sakurai reaction of an allylsilane with an azido-containing enone under Lewis acidic conditions followed by protonation of the resulting titanium enolate species allowed for a subsequent intramolecular Schmidt reaction. Alternatively, the intermediate titanium enolate could undergo an aldol reaction followed by the intramolecular Schmidt reaction to form lactam products with multiple stereogenic centers. The stereochemical features of the titanium enolate aldol reaction with several 3-azidoaldehyde substrates during this domino process is discussed.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Molecular Structure

Substances

  • Aldehydes
  • Anti-Bacterial Agents
  • Lactams
  • 3-hydroxybutanal