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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of 3,3'-spirocyclic oxindoles via phosphine catalyzed [4 + 2] cyclizations
Maxime Gicquel1, Catherine Gomez, Pascal Retailleau
1Institut de Chimie des Substances Naturelles, CNRS UPR 2301 - Centre de Recherche de Gif -1, avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Abstract:
Triphenylphosphine promoted reactions between 3-arylideneoxindoles and δ-aryl-substituted penta-2,3-dienoates afford an unprecedented access to spirocyclic oxindoles with functionalized six-membered rings. In these new [4 + 2] cyclization processes, the allenoates operate as the four-carbon synthons, thanks to the involvement of the substituted δ-carbons. These reactions give excellent control of the relative stereochemistry of the three stereogenic centers. The stereochemistry of the final product has been ascertained by X-ray diffraction studies.
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