Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 36, Pages 5069-5073Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800749
Keywords
Sulfinates; Organocatalysis; Allenyl sulfones; Lewis bases; Phase transfer
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Funding
- Region Normandie (CRUNCh network)
- Centre National de la Recherche Scientifique (CNRS)
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- INSA Rouen
- Rouen Normandy University
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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.
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