Cross-metathesis route to alkenyl AQ amides

Over the years we’ve experienced first-hand the frustrations of resorting to circuitous synthetic routes to access substituted alkenyl AQ amide substrates, which serve as cornerstones of AQ-directed alkene functionalization chemistry. To address this Hui-Qi, Zi-Qi, and Van teamed up to develop a concise and modular method using cross-metathesis with the Grubbs 2nd generation catalyst. Remarkably the catalyst is impervious to the AQ group, allowing direct coupling of terminal alkenyl AQ amides with a variety of terminal alkenes. In one case, we shorten a four-step sequence to a single high-yielding step. This paper is part of a special issue in Tetrahedron celebrating Prof. Guangbin Dong’s 2021 Tetrahedron Young Investigator Award. Well done team!

For a link to the paper, click here: