Alkenenitrile Transmissive Olefination: Synthesis of the Putative Lignan "Morinol I"

European J Org Chem. 2011 Dec;2011(34):6843-6846. doi: 10.1002/ejoc.201101235. Epub 2011 Oct 28.

Abstract

Grignard reagents trigger an addition-elimination with α'-hydroxy acrylonitriles to selectively generate Z-alkenenitriles. The modular assembly of Z-alkenenitriles from a Grignard reagent, acrylonitrile, and an aldehyde is ideal for stereoselectively synthesizing alkenes as illustrated in the synthesis of the putative lignan "morinol I."