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Asymmetric Sulfonylation from a Reaction of Cyclopropan-1-ol, Sulfur Dioxide, and 1-(Alkynyl)naphthalen-2-ol.

Chun ZhangShengqing YeJie Wu
Published in: Organic letters (2024)
Asymmetric sulfonylation from a reaction of cyclopropan-1-ol, sulfur dioxide, and 1-(alkynyl)naphthalen-2-ol in the presence of a catalytic amount of organocatalyst at room temperature is developed. Axially chiral ( S )-( E )-1-(1-(alkylsulfonyl)-2-arylvinyl)naphthalen-2-ols are generated in moderate to good yields with excellent enantioselectivity and regioselectivity under mild conditions. During this transformation, γ-keto sulfinate generated in situ from cyclopropan-1-ol and sulfur dioxide acts as the key intermediate.
Keyphrases
  • room temperature
  • ionic liquid
  • high intensity
  • mass spectrometry
  • crystal structure