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

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

Domains: Chemical Sciences; Organic chemistry

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, 2018, 360 (14), pp.2696-2706. ⟨10.1002/adsc.201800466⟩. ⟨hal-01850385⟩