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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.