Enantiospecific sp2–sp3 Coupling of ortho- and para-Phenols with Secondary and Tertiary Boronic Esters

Claire M. Wilson, Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)
210 Downloads (Pure)

Abstract

The coupling of ortho- and para-phenols with secondary and tertiary boronic esters has been explored. In the case of para-substituted phenols, after reaction of a dilithio phenolate species with a boronic ester, treatment with Ph3BiF2 or Martin's sulfurane gave the coupled product with complete enantiospecificity. The methodology was applied to the synthesis of the broad spectrum antibacterial natural product (−)-4-(1,5-dimethylhex-4-enyl)-2-methyl phenol. For ortho-substituted phenols, initial incorporation of a benzotriazole on the phenol oxygen atom was required. Subsequent ortho-lithiation and borylation gave the coupled product, again with complete stereospecificity.

Original languageEnglish
Pages (from-to)16318-16322
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number51
Early online date28 Nov 2017
DOIs
Publication statusPublished - 18 Dec 2017

Keywords

  • arylation
  • boronic esters
  • C−C bond formation
  • phenol
  • synthetic methods

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