Direct synthesis of polysubstituted aluminoisoxazoles and pyrazoles by a metalative cyclization

Org Lett. 2011 Oct 21;13(20):5664-7. doi: 10.1021/ol202389u. Epub 2011 Sep 26.

Abstract

Alumino-heteroles are obtained from simple precursors in a fully chemo- and regioselective manner by a metalative cyclization. The carbon-aluminum bond is still able to react further with several electrophiles, without the need of transmetalation. This synthetic route provides a novel entry to heterocyclic organoaluminum reagents as well as a straightforward access to 3,4,5-trisubstituted isoxazoles and 1,3,4,5-tetrasubstituted pyrazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum / chemistry*
  • Catalysis
  • Cyclization
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry

Substances

  • Isoxazoles
  • Organometallic Compounds
  • Pyrazoles
  • Aluminum