Synthesis of γ,δ-Unsaturated Esters and Amides via Au(I)-Catalyzed Reactions of Aryl Ynol Ethers or Ynamides with Allylic Alcohols

Souta Misawa, Asaki Miyairi, Yoshihiro Oonishi, Steven P. Nolan, Yoshihiro Sato*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, Email: biyopharm.hokudai.ac.jp

S. Misawa, A. Miyairi, Y. Oonoshi, S. P. Nolan, Y. Sato, Synthesis, 2021, 53, 4644-4645.

DOI: 10.1055/a-1559-3020

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Abstract

A Au(I)-catalyzed hydroalkoxylation/Claisen rearrangement cascade reaction of aryl ynol ethers and ynamides with allylic alcohols provides γ,δ-unsaturated esters or amides, respectively. The [Au(IPr)NTf₂] catalyst is most effective for this reaction, and the reaction proceeds under mild conditions in an atom-economical way.

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Key Words

gold catalysis, ynols, ynamides, hydrolysis, allylation, hydroalkoxylation, Claisen rearrangement, esters, amides,

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ID: J66-Y2021