Regiodirecting effects in difunctionalised tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts: building blocks for alkaloids

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.

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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 (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis (former - to 2025) 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:	18 Jun 2026 14:40
URI:	https://ueaeprints.uea.ac.uk/id/eprint/40717
DOI:	10.1016/j.tetlet.2012.09.086

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