(Z)-Selective Takai olefination of salicylaldehydes

The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of sal...

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Detalles Bibliográficos
Autores principales: Geddis, Stephen M, Hagerman, Caroline E, Galloway, Warren R J D, Sore, Hannah F, Goodman, Jonathan M, Spring, David R
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331342/
https://www.ncbi.nlm.nih.gov/pubmed/28326141
http://dx.doi.org/10.3762/bjoc.13.35
Descripción
Sumario:The Takai olefination (or Takai reaction) is a method for the conversion of aldehydes to vinyl iodides, and has seen widespread implementation in organic synthesis. The reaction is usually noted for its high (E)-selectivity; however, herein we report the highly (Z)-selective Takai olefination of salicylaldehyde derivatives. Systematic screening of related substrates led to the identification of key factors responsible for this surprising inversion of selectivity, and enabled the development of a modified mechanistic model to rationalise these observations.

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