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Chan Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr137

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Chan Rearrangement. Comprehensive Organic Name Reactions and Reagents. 624–626.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Chan rearrangement is a base-induced rearrangement of α-acyloxy-acetates to α-hydroxy-β-keto-esters and under similar conditions amino ketone can also be prepared. This reaction helps to assemble an array of three contiguous oxygenated carbons and has been applied to the syntheses of diazonamide A, aplasmomycin, boromycin, etc.

Keywords:

  • α-acyloxy-acetates;
  • α-hydroxy-β-keto-esters;
  • epoxide;
  • α-hydroxy-β-keto ester