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Synthesis of the Privileged 8‑Arylmenthol Class by Radical Arylation of Isopulegol

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journal contribution
posted on 13.05.2016, 18:34 by Steven W. M. Crossley, Ruben M. Martinez, Sebastián Guevara-Zuluaga, Ryan A. Shenvi
Hydrogen atom transfer (HAT) circumvents a disfavored Friedel–Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.