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Ferrier Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr228

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Ferrier Reaction. Comprehensive Organic Name Reactions and Reagents. 228:1046–1050.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Ferrier reaction is an acid-catalyzed or induced rearrangement of glycals in the presence of different nucleophiles (or aglycons). The acids used in this reaction include the protic acids, such as methanolic hydrochloric acid, sulfuric acid, and Lewis acids. Some neutral catalysts have also been developed for this reaction because substrates sensitive to acidic conditions are precluded. InCl3 has been found to possess superior catalytic activity relative to many other Lewis acid catalysts. Overall, this reaction has become an important synthetic tool, which predominantly produces α-anomer in good to excellent yield. This reaction has general applications in carbohydrate transformation.

Keywords:

  • protic acids;
  • InCl3;
  • SN1-type reaction;
  • Iodonium dicollidinium perchlorate