Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines
| Autor: | Jean-François Lohier, Thomas Martzel, Stéphane Perrio, Jean-François Brière, Annie-Claude Gaumont |
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| Rok vydání: | 2018 |
| Předmět: |
Annulation
010405 organic chemistry Chemistry Allene Organic Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Sulfone chemistry.chemical_compound Enantiopure drug Organocatalysis Propargyl Lewis acids and bases Physical and Theoretical Chemistry Isomerization |
| Zdroj: | European Journal of Organic Chemistry. 2018:5069-5073 |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201800749 |
| Popis: | The synthesis of 4‐sulfonyl‐3‐pyrrolines, from a propargylic sulfone and activated imines, is described. The annulation is initiated by sodium benzenesulfinate as organocatalyst, which allows isomerization of the alkynyl precursor to the analogous allene. A proof of concept towards an asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair was then highlighted (ee up to 41 %). An operationally simple methodology for the synthesis of 4‐sulfonyl‐3‐pyrrolines is described using a propargylic sulfone and N‐sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof‐of‐concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase‐transfer catalysts. |
| Databáze: | OpenAIRE |
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