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https://hdl.handle.net/2440/114036
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Type: | Journal article |
Title: | Cyclic enecarbamates as precursors of α,β-unsaturated iminium ions: reactivity and synthesis of 6,6-spirocyclic ring systems |
Other Titles: | Cyclic enecarbamates as precursors of alpha,beta-unsaturated iminium ions: reactivity and synthesis of 6,6-spirocyclic ring systems |
Author: | Wang, Z. Krogsgaard-Larsen, N. Daniels, B. Furkert, D. Brimble, M. |
Citation: | Journal of Organic Chemistry, 2016; 81(21):10366-10375 |
Publisher: | American Chemical Society |
Issue Date: | 2016 |
ISSN: | 0022-3263 1520-6904 |
Statement of Responsibility: | Zhanwei Wang, Niels Krogsgaard-Larsen, Benjamin Daniels, Daniel. P. Furkert and Margaret A. Brimble |
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. |
Rights: | © 2016 American Chemical Society |
DOI: | 10.1021/acs.joc.6b01343 |
Published version: | http://dx.doi.org/10.1021/acs.joc.6b01343 |
Appears in Collections: | Aurora harvest 3 IPAS publications |
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