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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of Spirocyclic Isoindolones Using an Alkynyl aza-Prins/Oxidative halo-Nazarov Cyclization Sequence
Jackson J Hernandez1, Alison J Frontier1
1Department of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York 14611, United States.
Abstract:
In this report, we describe an alkynyl halo-aza-Prins cyclization of 3-hydroxyisoindolones to prepare aza-Prins products. These Prins adducts undergo oxidation at the 3-isoindolone position after activation of the amide by triflic anhydride and 2-chloropyridine to form a pentadienyl cation capable of undergoing a halo-Nazarov cyclization. Using this methodology, angular-fused N-heterocyclic small molecules with two new rings, two new carbon-carbon bonds, a vinyl halide, and an aza-tertiary stereocenter can be obtained in good yields.
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