Asymmetric synthesis of 2-azabicyclo[3.3.1]nonanes by a microwave-assisted organocatalysed tandem desymmetrisation and intramolecular aldolisation

Org Biomol Chem. 2009 Jun 21;7(12):2517-9. doi: 10.1039/b906835j. Epub 2009 May 18.

Abstract

The six-membered nitrogen-containing ring of the morphan scaffold, ubiquitous in natural products, is formed by an intramolecular aldol process of an aza-tethered dicarbonyl compound, leading to the first asymmetric synthesis of a morphan derivative using organocatalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Azabicyclo Compounds / chemical synthesis*
  • Azabicyclo Compounds / chemistry
  • Catalysis
  • Glycine / analogs & derivatives
  • Glycine / chemistry
  • Ketones / chemistry
  • Microwaves*
  • Proline / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Aldehydes
  • Azabicyclo Compounds
  • Ketones
  • 2-aminoacetaldehyde
  • 3-hydroxybutanal
  • Proline
  • Glycine