Palladium-mediated fragmentation reactions of meta photocycloadducts to afford arylated or oxidatively cyclised products
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...
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| Published in | Tetrahedron Vol. 62; no. 40; pp. 9403 - 9409 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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02.10.2006
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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 π-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 π-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.
[Display omitted] |
|---|---|
| AbstractList | 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 π-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 π-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.
[Display omitted] 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 pi-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 pi-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. (c) 2006 Elsevier Ltd. All rights reserved. |
| Author | Byrne, Paul W. Berritt, Simon Penkett, Clive S. Sims, Rupert O. Pennicott, Lewis E. Rushton, Stephen P. Hitchcock, Peter B. Avent, Anthony G. |
| Author_xml | – sequence: 1 givenname: Clive S. surname: Penkett fullname: Penkett, Clive S. email: c.s.penkett@sussex.ac.uk organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK – sequence: 2 givenname: Rupert O. surname: Sims fullname: Sims, Rupert O. organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK – sequence: 3 givenname: Paul W. surname: Byrne fullname: Byrne, Paul W. organization: Tocris-Cookson Ltd, Avonmouth, Bristol BS11 8TA, UK – sequence: 4 givenname: Simon surname: Berritt fullname: Berritt, Simon organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK – sequence: 5 givenname: Lewis E. surname: Pennicott fullname: Pennicott, Lewis E. organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK – sequence: 6 givenname: Stephen P. surname: Rushton fullname: Rushton, Stephen P. organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK – sequence: 7 givenname: Anthony G. surname: Avent fullname: Avent, Anthony G. organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK – sequence: 8 givenname: Peter B. surname: Hitchcock fullname: Hitchcock, Peter B. organization: Department of Chemistry, University of Sussex, Brighton BN1 9QJ, UK |
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| Cites_doi | 10.1021/cr020027w 10.1021/cr020039h 10.1021/ja015791z 10.1016/j.tet.2005.04.002 10.1002/anie.200351196 10.1002/anie.199423791 10.1021/cr9903048 10.1039/b404816d 10.1021/ja015827n 10.1016/j.tet.2006.01.042 10.1021/ar00170a006 10.1016/S0040-4020(99)00263-X 10.1021/ja983617d 10.1039/a827427z 10.1016/S0040-4039(01)80544-X 10.1039/CO9960300447 10.1021/cr9409804 10.1021/ja9701366 10.1002/anie.200390048 10.1016/S0040-4020(00)00438-5 |
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| Keywords | ALCOHOLS STONE INTRAMOLECULAR HECK REACTION CATALYZED ALLYLIC ALKYLATIONS CYCLIZATION MOLECULAR-OXYGEN |
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| Snippet | Whilst seeking to improve the yield of a Heck-style arylation/fragmentation reaction using a silyloxy substituted
meta photocycloadduct, an alternative... Whilst seeking to improve the yield of a Heck-style arylation/fragmentation reaction using a silyloxy substituted meta photocycloadduct, an alternative... |
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| Title | Palladium-mediated fragmentation reactions of meta photocycloadducts to afford arylated or oxidatively cyclised products |
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