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

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.

SUBMITTER: Crossley SW 

PROVIDER: S-EPMC5871529 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature