Gold Catalysis: Synthesis of 3‐Acylindenes from 2‐Alkynylaryl Epoxides | Zendy

Hashmi A. Stephen K. | Zendy; Bührle Miriam | Zendy; Salathé Ralph | Zendy; Bats Jan W. | Zendy

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Gold Catalysis: Synthesis of 3‐Acylindenes from 2‐Alkynylaryl Epoxides

Author(s) -

Hashmi A. Stephen K.,

Bührle Miriam,

Salathé Ralph,

Bats Jan W.

Publication year - 2008

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200800385

Subject(s) - chemistry , epoxide , isomerization , intramolecular force , ketone , sonogashira coupling , wittig reaction , catalysis , organic chemistry , palladium

A series of 2‐alkynylaryl epoxides were prepared by a sequence of Sonogashira coupling, Wittig olefination and epoxidation or a Darzens’ glycid ester synthesis. The conversion of these substrates with gold(I) catalysts furnished 3‐acylindenes and, in occasional cases as side‐products, the products of an isomerization of the oxirane ring to a ketone. Isotope labelling of the epoxide oxygen indicates an intramolecular oxygen transfer.

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