Gold-Catalyzed Dehydrogenative Cycloisomerization of 1,4-Enyne Esters to 3,5-Disubstituted Phenol Derivatives

Cuili Chen, Xianxiao Chen, Xiaoxiang Zhang, Shifa Wang, Weidong Rao, Philip Wai Hong Chan

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9 Citations (Scopus)

Abstract

A method to prepare synthetically important 3,5-disubstituted phenol derivatives that relies on the sequential gold(I)-catalyzed dehydrogenative cycloisomerization of 1,4-enyne esters in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) or N-fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram-scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771.

Original languageEnglish
Pages (from-to)4359-4368
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number24
DOIs
Publication statusPublished - 19 Dec 2017

Keywords

  • 1,4-enyne esters
  • 3,5-disubstituted phenols
  • dehydrogenative cycloisomerization
  • gold
  • homogeneous catalysis

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