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Feldman AW, Ovaska SI, Ovaska TV. Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence. Tetrahedron. 2014;70(27):4147-4155doi: 10.1016/j.tet.2014.02.089.
Feldman, A. W., Ovaska, S. I., & Ovaska, T. V. (2014). Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence. Tetrahedron, 70(27), 4147-4155. https://doi.org/10.1016/j.tet.2014.02.089
Feldman, Aaron W, et al. "Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence." Tetrahedron vol. 70,27 (2014): 4147-4155. doi: https://doi.org/10.1016/j.tet.2014.02.089
Feldman AW, Ovaska SI, Ovaska TV. Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence. Tetrahedron. 2014 Jul 08;70(27):4147-4155. doi: 10.1016/j.tet.2014.02.089. PMID: 24994941; PMCID: PMC4074778.
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Tetrahedron. 2014 Jul 08;70(27):4147-4155. doi: 10.1016/j.tet.2014.02.089.

Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence.

Tetrahedron

Aaron W Feldman, Sami I Ovaska, Timo V Ovaska

Affiliations

  1. Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, United States of America.

PMID: 24994941 PMCID: PMC4074778 DOI: 10.1016/j.tet.2014.02.089

Abstract

Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.

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