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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
Author(s) -
Martzel Thomas,
Lohier JeanFrançois,
Gaumont AnnieClaude,
Brière JeanFrançois,
Perrio Stéphane
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800466
Subject(s) - chemistry , annulation , ammonium , sulfonyl , alkyl , adduct , aryl , phase (matter) , organocatalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , enantioselective synthesis
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.