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  • Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol.

Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol.

Organic letters (2016-05-14)
Steven W M Crossley, Ruben M Martinez, Sebastián Guevara-Zuluaga, Ryan A Shenvi
PMID27175746
ABSTRACT

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.