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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement
Aaron W Feldman1, Sami I Ovaska1, Timo V Ovaska1
1Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, United States of America.
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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