Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives.

Beilstein J Org Chem

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 MeiLong Road, Shanghai 200237, People's Republic of China.

Published: November 2013

AI Article Synopsis

  • Oxabicyclic alkenes react with electron-deficient terminal alkynes in mild conditions using a gold catalyst to yield addition products in moderate yields.
  • When alkynyl esters are the substrate, the resulting products are (Z)-acrylate derivatives.
  • Using but-3-yn-2-one leads to an addition product with an (E)-configuration, and the text also discusses the mechanism behind these reactions.

Article Abstract

Oxabicyclic alkenes can react with electron-deficient terminal alkynes in the presence of a gold catalyst under mild conditions, affording the corresponding addition products in moderate yields. When using alkynyl esters as substrates, the (Z)-acrylate derivatives are obtained. Using but-3-yn-2-one (ethynyl ketone) as a substrate, the corresponding addition product is obtained with (E)-configuration. The proposed mechanism of these reactions is also discussed.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817539PMC
http://dx.doi.org/10.3762/bjoc.9.233DOI Listing

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