Synthesis of <i>E</i>-Dienyl Esters Using Acetylene as C2 Synthon
Boxiang Liu, Zhicong Lin, Tairan Cheng, Tongxiang Cao, Shifa Zhu
Abstract
The stereoselective synthesis of dienyl esters with high atom- and step-economy has been largely unexplored. Herein, we report an efficient approach for the synthesis of E -dienyl esters via rhodium catalysis using carboxylic acid and acetylene as C2 synthon through the cascade of cyclometalation and C–O coupling. This protocol features mild conditions, excellent functional group tolerance, and exclusive E -stereoselectivity and utility in the late-stage modification of pharmaceuticals and natural products.
Topics & Concepts
SynthonChemistryStereoselectivityAcetyleneAtom economyCatalysisCombinatorial chemistryOrganic chemistryAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions