Iron-Catalyzed Hydrobenzylation: Stereoselective Synthesis of (−)-Eugenial C
Xu-cheng Gan, Simona Kotesova, Alberto Castanedo, Samantha A. Green, S. Möller, Ryan A. Shenvi
Abstract
Metal-hydride hydrogen atom transfer (MHAT) has emerged as a useful tool to form quaternary carbons from alkenes via hydrofunctionalization. Methods to date that cross-couple alkenes with sp 3 partners rely on heterobimetallic catalysis to merge the two cycles. Here, we report an iron-only cross-coupling via putative MHAT/S H 2 steps that solves a key stereochemical problem in the synthesis of meroterpenoid eugenial C and obviates the need for nickel. The concise synthesis benefits from a conformationally locked o,o′- disubstituted benzyl bromide and a locally sourced chiral pool terpene coupling partner.
Topics & Concepts
ChemistryStereoselectivityBromideHydrideCatalysisCombinatorial chemistryNickelMerge (version control)MetalStereochemistryEnantioselective synthesisStereoisomerismOrganic chemistryComputer scienceInformation retrievalCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsAlkaloids: synthesis and pharmacology