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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
Statement of
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
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