1. Synthesis of 3,3'-spirocyclic oxindoles via phosphine catalyzed [4 + 2] cyclizations
- Author
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Arnaud Voituriez, Maxime Gicquel, Catherine Gomez, Angela Marinetti, Pascal Retailleau, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Indoles ,Phosphines ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Catalysis ,Stereocenter ,chemistry.chemical_compound ,Organophosphorus Compounds ,X-Ray Diffraction ,Organic chemistry ,Spiro Compounds ,Physical and Theoretical Chemistry ,Triphenylphosphine ,Molecular Structure ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Organic Chemistry ,Synthon ,Stereoisomerism ,0104 chemical sciences ,Oxindoles ,chemistry ,Cyclization ,Phosphine - Abstract
International audience; 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.
- Published
- 2013
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