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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

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

Crossley Steven W M SW Martinez Ruben M RM Guevara-Zuluaga Sebastián S Shenvi Ryan A RA

Organic letters 20160513 11

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. ...[more]

PMID: 27175746

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