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Wang Z, Krogsgaard-Larsen N, Daniels B, et al. Cyclic Enecarbamates as Precursors of α,β-Unsaturated Iminium Ions: Reactivity and Synthesis of 6,6-Spirocyclic Ring Systems. J Org Chem. 2016;81(21):10366-10375doi: 10.1021/acs.joc.6b01343.
Wang, Z., Krogsgaard-Larsen, N., Daniels, B., Furkert, D. P., & Brimble, M. A. (2016). Cyclic Enecarbamates as Precursors of α,β-Unsaturated Iminium Ions: Reactivity and Synthesis of 6,6-Spirocyclic Ring Systems. The Journal of organic chemistry, 81(21), 10366-10375. https://doi.org/10.1021/acs.joc.6b01343
Wang, Zhanwei, et al. "Cyclic Enecarbamates as Precursors of α,β-Unsaturated Iminium Ions: Reactivity and Synthesis of 6,6-Spirocyclic Ring Systems." The Journal of organic chemistry vol. 81,21 (2016): 10366-10375. doi: https://doi.org/10.1021/acs.joc.6b01343
Wang Z, Krogsgaard-Larsen N, Daniels B, Furkert DP, Brimble MA. Cyclic Enecarbamates as Precursors of α,β-Unsaturated Iminium Ions: Reactivity and Synthesis of 6,6-Spirocyclic Ring Systems. J Org Chem. 2016 Nov 04;81(21):10366-10375. doi: 10.1021/acs.joc.6b01343. Epub 2016 Aug 01. PMID: 27441647.
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J Org Chem. 2016 Nov 04;81(21):10366-10375. doi: 10.1021/acs.joc.6b01343. Epub 2016 Aug 01.

Cyclic Enecarbamates as Precursors of α,β-Unsaturated Iminium Ions: Reactivity and Synthesis of 6,6-Spirocyclic Ring Systems.

The Journal of organic chemistry

Zhanwei Wang, Niels Krogsgaard-Larsen, Benjamin Daniels, Daniel P Furkert, Margaret A Brimble

Affiliations

  1. School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
  2. Maurice Wilkins Centre for Molecular Biodiscovery , 3 Symonds Street, Auckland 1142, New Zealand.

PMID: 27441647 DOI: 10.1021/acs.joc.6b01343

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.

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