Accessing Enantiopure Endocyclic Sulfoximines Through Catalytic Cycloisomerization of Oxygenated Propargyl‐Sulfinamides

In this study, a novel strategy to access endocyclic sulfoximines in an enantiopure form is reported. The approach is based on a silver nitrate‐catalyzed cyclo‐isomerization reaction of oxygenated propargylic sulfinamides and provides efficiently 5‐membered endocyclic sulfoximines (isothiazole 1‐oxi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-03, Vol.361 (6), p.1236-1240
Main Authors: Cividino, Pascale, Verrier, Charlie, Philouze, Christian, Carret, Sébastien, Poisson, Jean‐François
Format: Article
Language:English
Subjects:
Acetylenic ethers
Catalysis
Chemical Sciences
Cyclization
Dealkylation
Homogenous catalysis
Isomerization
Lewis acid
Oxygenation
Silver
Sulfinamide
Sulfoximine
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Summary:In this study, a novel strategy to access endocyclic sulfoximines in an enantiopure form is reported. The approach is based on a silver nitrate‐catalyzed cyclo‐isomerization reaction of oxygenated propargylic sulfinamides and provides efficiently 5‐membered endocyclic sulfoximines (isothiazole 1‐oxide). These new heterocyclic scaffolds can be isolated or directly converted into cyclic sulfinamides via Lewis acid‐mediated sulfur dealkylation reactions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801408