Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes

J Org Chem. 2011 Dec 2;76(23):9792-800. doi: 10.1021/jo2018922. Epub 2011 Nov 1.

Abstract

Photochemical oxa-di-π-methane rearrangement of bicyclo[3.2.1]octanoid scaffolds affords multifunctional, donor-acceptor cyclopropanes. A related photochemical reaction of an iminium ether substrate uncovered an unprecedented aza-di-π-methane rearrangement of a β,γ-unsaturated iminium. Donor-acceptor cyclopropanes have been evaluated as substrates for reactions generating several new chemotypes.

Publication types

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

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Crystallography, X-Ray
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds
  • Cyclopropanes