(Z)-Selective Takai olefination of salicylaldehydes

oleh: Stephen M. Geddis, Caroline E. Hagerman, Warren R. J. D. Galloway, Hannah F. Sore, Jonathan M. Goodman, David R. Spring

Format: Article
Diterbitkan: Beilstein-Institut 2017-02-01

Deskripsi

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.