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Accessing Enantiopure Endocyclic Sulfoximines Through Catalytic Cycloisomerization of Oxygenated Propargyl‐Sulfinamides
Author(s) -
Cividino Pascale,
Verrier Charlie,
Philouze Christian,
Carret Sébastien,
Poisson JeanFrançois
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801408
Subject(s) - enantiopure drug , cycloisomerization , chemistry , propargyl , isomerization , catalysis , alkylation , organic chemistry , combinatorial chemistry , enantioselective synthesis
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.