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Kennedy Oxidative Cyclization

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr358

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Kennedy Oxidative Cyclization. Comprehensive Organic Name Reactions and Reagents. 358:1609–1612.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Kennedy oxidative cyclization is a highly stereoselective conversion of 5-hydroxyl alkene into a trans-tetrahydrofuran derivative with erythro stereochemistry at the two vicinal carbinol centers via rhenium (VII) oxide (Re2O7) promoted syn-oxidative cyclization. The study finds that this reaction is powerful in converting polyenes into polyoxygenated chiral derivatives, particularly in combination with the sharpless asymmetric oxidation. This reaction has been successfully applied for the synthesis of acetogenins and tetrahydrofuran derivatives.

Keywords:

  • 5-hydroxyl alkene;
  • acetogenins;
  • rhenium (VII) oxide (Re2O7);
  • tetrahydrofuran derivatives