Palladium-mediated fragmentation reactions of meta photocycloadducts to afford arylated or oxidatively cyclised products

Penkett, Clive S, Sims, Rupert O, Byrne, Paul W, Berritt, Simon, Pennicott, Lewis E, Rushton, Stephen P, Avent, Anthony G and Hitchcock, Peter B (2006) Palladium-mediated fragmentation reactions of meta photocycloadducts to afford arylated or oxidatively cyclised products. Tetrahedron, 62 (40). pp. 9403-9409. ISSN 0040-4020

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Abstract

Whilst seeking to improve the yield of a Heck-style arylation/fragmentation reaction using a silyloxy substituted meta photocycloadduct, an alternative reaction pathway was discovered that led to the formation of the unique oxidatively cyclised compound 8. This tricyclic ether is believed to form as the result of the meta photocycloadduct structure fragmenting to give a -allyl palladium species and then subsequently being displaced by a neighbouring hydroxyl group. An attempt to develop an enantioselective version of this reaction via the desymmetrisation of a meso -allyl palladium intermediate was made using the meta photocycloadduct derived from anisole and Z-but-2-ene-1,4-diol, however no enantioenrichment of the products could be detected.

Item Type: Article
Additional Information: (with Clive S. Penkett, Rupert O. Sims, Paul W. Byrne, Simon Berritt, Stephen P. Rushton, Anthony G. Avent and Peter B. Hitchcock)
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Clive Penkett
Date Deposited: 06 Feb 2012 21:20
Last Modified: 17 Jul 2013 13:05
URI: http://sro.sussex.ac.uk/id/eprint/30816
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