title: 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.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Steven W M
authors.initials: SW
authors.lastname: Crossley
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ruben M
authors.initials: RM
authors.lastname: Martinez
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Sebastián
authors.initials: S
authors.lastname: Guevara-Zuluaga
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Shenvi
mesh_terms: D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D003510:Cyclohexanes / Q000138:chemical synthesis*; D005609:Free Radicals / Q000737:chemistry; D008610:Menthol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism; D013464:Sulfuric Acids / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry*
chemical_list: C435306:8-phenylmenthol; D000081005:Cyclohexane Monoterpenes; D003510:Cyclohexanes; D005609:Free Radicals; D013464:Sulfuric Acids; D013729:Terpenes; D008610:Menthol; C409816:isopulegol; C033158:sulfuric acid