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https://hdl.handle.net/2440/114036
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dc.contributor.author | Wang, Z. | - |
dc.contributor.author | Krogsgaard-Larsen, N. | - |
dc.contributor.author | Daniels, B. | - |
dc.contributor.author | Furkert, D. | - |
dc.contributor.author | Brimble, M. | - |
dc.date.issued | 2016 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2016; 81(21):10366-10375 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.issn | 1520-6904 | - |
dc.identifier.uri | http://hdl.handle.net/2440/114036 | - |
dc.description.abstract | The scalable synthesis of cyclic enecarbamates and their use as convenient precursors of α,β-unsaturated N-acyl iminium ions is reported. The newly developed route overcomes synthetic and reactivity difficulties in previously reported methods, is readily scaled up, and proceeds through stable intermediates suitable for long-term storage if required. Preliminary investigations probing the reactivity of cyclic α,β-unsaturated N-acyl iminium ions as dienophiles in Diels-Alder reactions and electrophilic alkylating agents are described. In the presence of Lewis and Brønsted acids, iminium precursor 22a underwent efficient Diels-Alder cycloaddition with a range of simple and complex dienes, culminating in the synthesis of 6,6-spirocyclic ring systems possessing the same relative stereochemistry as the spirocyclic imine present in the marine natural product gymnodimine 1. | - |
dc.description.statementofresponsibility | Zhanwei Wang, Niels Krogsgaard-Larsen, Benjamin Daniels, Daniel. P. Furkert and Margaret A. Brimble | - |
dc.language.iso | en | - |
dc.publisher | American Chemical Society | - |
dc.rights | © 2016 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/acs.joc.6b01343 | - |
dc.title | Cyclic enecarbamates as precursors of α,β-unsaturated iminium ions: reactivity and synthesis of 6,6-spirocyclic ring systems | - |
dc.title.alternative | Cyclic enecarbamates as precursors of alpha,beta-unsaturated iminium ions: reactivity and synthesis of 6,6-spirocyclic ring systems | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/acs.joc.6b01343 | - |
pubs.publication-status | Published | - |
Appears in Collections: | Aurora harvest 3 IPAS publications |
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