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Sulfinate-Organocatalyzed (3+2) Annulation of Allenyl Sulfones with 1,1-Dicyano Olefins in the Presence of a Quaternary Ammonium Phase Transfer Agent

Thomas Martzel 1 Jean-François Lohier 1 Annie-Claude Gaumont 1 Jean-François Brière 2 Stéphane Perrio 1
1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : The benzenesulfinate‐catalyzed (3+2) annulation between allenyl sulfones and aryl(alkyl)idenemalononitriles has been developed under mild phase transfer conditions, affording a breadth of functionalized sulfonyl cyclopentenes in good to excellent yields (22 examples, 49–99%) and high diastereoselectivities. These adducts were likely generated, via an allylsulfone anion featuring a quaternary ammonium cation.
Keywords : phase-transfer catalysis sulfinate annulation allene carbocycle
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01850385
Contributor : Jocelyne Levillain Connect in order to contact the contributor
Submitted on : Friday, July 27, 2018 - 11:54:29 AM
Last modification on : Tuesday, January 4, 2022 - 4:20:36 AM

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COMUE-NORMANDIE | CNRS | INSA-ROUEN | INC-CNRS | UNIROUEN | ENSICAEN | UNICAEN | LCMT | COBRA | INSA-GROUPE | UNILEHAVRE

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Thomas Martzel, Jean-François Lohier, Annie-Claude Gaumont, Jean-François Brière, Stéphane Perrio. Sulfinate-Organocatalyzed (3+2) Annulation of Allenyl Sulfones with 1,1-Dicyano Olefins in the Presence of a Quaternary Ammonium Phase Transfer Agent. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2018, 360 (14), pp.2696-2706. ⟨10.1002/adsc.201800466⟩. ⟨hal-01850385⟩

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