TiCl4-promoted tandem carbonyl or imine addition and Friedel-Crafts cyclization: synthesis of benzo-fused oxabicyclooctanes and nonanes

Org Lett. 2012 Apr 20;14(8):2002-5. doi: 10.1021/ol300494q. Epub 2012 Apr 4.

Abstract

A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl(4)-mediated tandem carbonyl or imine addition followed by a Friedel-Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.

Publication types

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

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Cycloparaffins / chemical synthesis*
  • Cycloparaffins / chemistry
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Alkanes
  • Bridged Bicyclo Compounds, Heterocyclic
  • Cycloparaffins
  • Furans
  • titanium tetrachloride
  • Titanium
  • nonane