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Juliá-Colonna Asymmetric Epoxidation

(Juliá Asymmetric Epoxidation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr352

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Juliá-Colonna Asymmetric Epoxidation. Comprehensive Organic Name Reactions and Reagents. 352:1583–1587.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The oxidation of electron-deficient trans-α,β-enones into trans-α,β-epoxyketones by a hydroperoxide anion in the presence of polyamino acid is known as the Juliá epoxidation. However, it is more generally referred to as the Juliá–Colonna asymmetric epoxidation. The initial epoxidation protocol is limited to electron-deficient enones, such as chalcone in a three-phase reaction and this protocol has been further extended to a two-phase reaction by dissolving enones in THF and using anhydrous urea-H2O2 as an oxidant in the presence of insoluble polyamino acid. Besides this several other modification for this reaction have been suggested. It has also been found that immobilizing the catalyst on silica gel bears advantages. This reaction has been applied for the epoxidation of trans-enones.

Keywords:

  • hydroperoxide anion;
  • poly-neopentylglycine;
  • polyethylene glycol (PEG);
  • sodium percarbonate