Highly Efficient and Eco-friendly Gold-Catalyzed Synthesis of Homoallylic Ketones

Adrian Gomez Suarez, Danila Gasperini, Sai Vummaleti, Albert Poater, Luigi Cavallo, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)

Abstract

We report a new catalytic protocol for the synthesis of γ,δ−unsaturated carbonyl units from simple starting
materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more
efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique.
In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in
order to shed light on how the Claisen rearrangement is initiated.
Original languageEnglish
Pages (from-to)2701-2705
Number of pages5
JournalACS Catalysis
Volume4
Early online date15 Jul 2014
DOIs
Publication statusPublished - 2014

Keywords

  • gold, hydroalkoxylation, Claisen rearrangement, homoallylic ketones, solvent-free

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