Catalytic Enantioselective Intermolecular Three-Component Sulfenylative Difunctionalizations of 1,3-Dienes

This work demonstrates regio- and enantioselective intermolecular three-component oxysulfenylations of 1,3-dienes with alcohols, phenols, acids, and water as O-nucleophiles. These reactions were enabled by the cooperative catalysis of chiral sulfide and phosphoric acid. Various useful sulfur-contain...

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Bibliographic Details
Published inACS catalysis Vol. 13; no. 4; pp. 2715 - 2722
Main Authors Liu, Xiao-Dong, Ye, Ai-Hui, Chen, Zhi-Min
Format Journal Article
LanguageEnglish
Published American Chemical Society 17.02.2023
Subjects
homoallylic sulfide
sulfenylation
multicomponent reaction
1,3-diene
cooperative catalysis
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Summary:This work demonstrates regio- and enantioselective intermolecular three-component oxysulfenylations of 1,3-dienes with alcohols, phenols, acids, and water as O-nucleophiles. These reactions were enabled by the cooperative catalysis of chiral sulfide and phosphoric acid. Various useful sulfur-containing allylic ethers, allylic esters, and allylic alcohols were readily obtained in moderate to excellent yields with high to excellent enantioselectivities and excellent regioselectivities. This protocol provides high chemo-, regio-, and enantioselectivities together with a broad scope and good functional group compatibility.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c05440