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Synthesis and reactivity of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones
Authors:Gopal Bose
Institution:Institut für Chemie und Biochemie der Ernst-Moritz-Arndt Universität Greifswald, Soldmannstr. 16, D-17487 Greifswald, Germany
Abstract:The first 1-hydroxyspiro2.5]cyclooct-4-en-3-ones were prepared by cyclization of free and masked 1,3-dicarbonyl dianions with 1,1-diacetylcyclopropane. 1-Hydroxyspiro2.5]cyclooct-4-en-3-ones represent precursors of unstable spiro5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. The reactions are enhanced by dynamic spiro-activation.
Keywords:Cyclizations  Cyclopropanes  Domino reactions  Spiro compounds  Silyl enol ethers
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