Literature DB >> 27175746

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

Steven W M Crossley1, Ruben M Martinez1, Sebastián Guevara-Zuluaga1, Ryan A Shenvi1.   

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.

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Year:  2016        PMID： 27175746      PMCID： PMC5871529          DOI： 10.1021/acs.orglett.6b01047

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  40 in total

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