Hydrotalcite catalysis for the synthesis of new chiral building blocks

Nat Prod Res. 2016;30(7):834-40. doi: 10.1080/14786419.2015.1075525. Epub 2015 Oct 9.

Abstract

The use of hydrotalcites for the synthesis of two chiral building blocks in a simple way is described as a new and green methodology. The synthesis of these compounds implies a regioselective Baeyer-Villiger reaction in a very selective way with ulterior opening and lactonisation. This methodology should be considered green for the use of hydrogen peroxide as the only oxidant and hydrotalcites as the catalyst, and because no residues are produced apart from water. The procedure is very adequate for using in gram scale, in order to increase the value of the obtained compounds. The conditions are excellent and can be applied for nonstable compounds, as they are very mild. The synthesised compounds are magnific starting materials for the synthesis of biologically active or natural compounds. The use of a cheap, commercial and chiral compound as carvone disposable in both enantiomeric forms adds an extra value to this methodology.

Keywords: Hydrotalcites; carvone; hydrogen peroxide; natural products; terpenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum Hydroxide / chemistry*
  • Catalysis
  • Cyclohexane Monoterpenes
  • Green Chemistry Technology*
  • Hydrogen Peroxide / chemistry
  • Magnesium Hydroxide / chemistry*
  • Monoterpenes / chemistry*
  • Oxidants / chemistry
  • Stereoisomerism

Substances

  • Cyclohexane Monoterpenes
  • Monoterpenes
  • Oxidants
  • hydrotalcite
  • Aluminum Hydroxide
  • carvone
  • Hydrogen Peroxide
  • Magnesium Hydroxide