Phosphine-catalyzed reactions of activated olefins tethered to cycloalkanones. substrate- and solvent-controlled synthesis of bicyclo[3.2.1]octanones, mixed acetals, and Morita-Baylis-Hillman products

Org Lett. 2013 Dec 20;15(24):6198-201. doi: 10.1021/ol403039b. Epub 2013 Nov 11.

Abstract

The n-Bu3P organocatalyzed reaction of cycloalkanones, i.e., cyclopentanones or 1,3-cyclopentanediones tethered to actived olefins, afforded selectively and in high yields three different types of products: bicyclo[3.2.1]octanones, mixed acetals, and Morita-Baylis-Hillman products. The progress of the reaction was closely related to the reaction medium and to the length of the tether located between the cyclopentanone (-dione) and the activated olefin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemical synthesis*
  • Acetals / chemistry
  • Alkenes / chemistry*
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Catalysis
  • Molecular Structure
  • Phosphines / chemistry*
  • Solvents / chemistry

Substances

  • Acetals
  • Alkenes
  • Bridged Bicyclo Compounds
  • Phosphines
  • Solvents
  • phosphine