Synthesis of 2-azaspiro[4.6]undec-7-enes from N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

J Org Chem. 2012 Nov 2;77(21):9707-17. doi: 10.1021/jo301764g. Epub 2012 Oct 25.

Abstract

The FeCl(3)-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Cyclohexanols / chemical synthesis*
  • Cyclohexanols / chemistry*
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism
  • Tosyl Compounds / chemical synthesis*
  • Tosyl Compounds / chemistry*

Substances

  • Cyclohexanols
  • Spiro Compounds
  • Tosyl Compounds