Geddis Stephen M, Hagerman Caroline E, Galloway Warren R J D, Sore Hannah F, Goodman Jonathan M, Spring David R
Department of Chemistry, University of Cambridge, Lensfield Rd, Cambridge, CB2 1EW, UK.
Beilstein J Org Chem. 2017 Feb 20;13:323-328. doi: 10.3762/bjoc.13.35. eCollection 2017.
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 ()-selectivity; however, herein we report the highly ()-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.
高井烯化反应（或高井反应）是一种将醛转化为乙烯基碘的方法，已在有机合成中广泛应用。该反应通常以其高（）选择性而闻名；然而，在此我们报道了水杨醛衍生物的高（）选择性高井烯化反应。对相关底物的系统筛选导致确定了导致这种令人惊讶的选择性反转的关键因素，并能够开发一种改进的机理模型来合理化这些观察结果。
