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Iron-Catalyzed Hydrobenzylation: Stereoselective Synthesis of (-)-Eugenial C
Xu-Cheng Gan1, Simona Kotesova1,2, Alberto Castanedo1
1Department of Chemistry, Scripps Research, La Jolla, California 92037, United States.
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 sp3 partners rely on heterobimetallic catalysis to merge the two cycles. Here, we report an iron-only cross-coupling via putative MHAT/SH2 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.
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