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Eschenmoser Coupling

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr218

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Eschenmoser Coupling. Comprehensive Organic Name Reactions and Reagents. 218:1001–1004.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The formation of vinylogous amides and urethanes by alkylation of secondary or tertiary thioamides with an electrophilic reagent followed by the extrusion of sulfur is known as the Eschenmoser coupling. Essentially, this reaction is analogous to the aza Claisen-Schmidt Condensation; however, it is not well suited for introducing the meso substituents. This reaction has been used for the preparation of vinylogous amides, especially for vitamin B12.

Keywords:

  • vitamin B12;
  • urethanes;
  • vinyl thioether;
  • vinylogous amides