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Stephenson, G. Richard 
ORCID: https://orcid.org/0000-0003-1487-9178 and Palotai, Ian M.
(2013)
Regiodirecting effects in difunctionalised tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts: building blocks for alkaloids.
Tetrahedron Letters, 54 (2).
pp. 123-127.
Abstract
Electrophilic tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts that incorporate methoxy and 2-ethanoyl ester substituents have been prepared, and the regiochemistry of their reactions with nucleophiles in arylation reactions has been examined using the model nucleophile diphenylzinc. The 1-carbomethoxymethyl-2-methoxy salt 1 reacts selectively by the ω addition pathway, but the 2-carbomethoxymethyl-3-methoxy salt 9 gave a 6:1 mixture of ω and α addition products. The 1-carbomethoxymethyl-2-methoxy regioisomer 1 was prepared in >95% purity without recourse to chromatography and shows the correct regiocontrol for use as a starting material in organoiron-mediated routes to alkaloids such as lycorine and parkacine.
| Item Type: | Article |
|---|---|
| Faculty \ School: | Faculty of Science > School of Chemistry |
| UEA Research Groups: | Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) |
| Depositing User: | Users 2731 not found. |
| Date Deposited: | 08 Jan 2013 13:06 |
| Last Modified: | 31 Oct 2022 16:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/40717 |
| DOI: | 10.1016/j.tetlet.2012.09.086 |
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