Asymmetric Sulfonylation from a Reaction of Cyclopropan-1-ol, Sulfur Dioxide, and 1-(Alkynyl)naphthalen-2-ol
Chun Zhang, Shengqing Ye, Jie Wu
Abstract
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.
Topics & Concepts
ChemistrySulfur dioxideRegioselectivityCatalysisSulfurMedicinal chemistryOrganic chemistrySulfur-Based Synthesis TechniquesAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and Catalysis