Generation of Oxazolidine‐2,4‐diones Bearing Sulfur‐Substituted Quaternary Carbon Atoms by Oxothiolation/Cyclization of Ynamides | Zendy

Huang Hai | Zendy; Fan Junzhen | Zendy; He Guangke | Zendy; Yang Zhimin | Zendy; Jin Xiaodong | Zendy; Liu Qi | Zendy; Zhu Hongjun | Zendy

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Generation of Oxazolidine‐2,4‐diones Bearing Sulfur‐Substituted Quaternary Carbon Atoms by Oxothiolation/Cyclization of Ynamides

Author(s) -

Huang Hai,

Fan Junzhen,

He Guangke,

Yang Zhimin,

Jin Xiaodong,

Liu Qi,

Zhu Hongjun

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201504356

Subject(s) - sulfur , bearing (navigation) , quaternary , oxazolidine , carbon fibers , quaternary carbon , chemistry , organic chemistry , materials science , geology , computer science , paleontology , catalysis , composite material , enantioselective synthesis , artificial intelligence , composite number

A novel method for metal‐free oxothiolation of ynamides to construct oxazolidine‐2,4‐diones bearing sulfur‐substituted quaternary carbon atoms has been developed. It represents a rare C−O bond cleavage of ynamides, as well as a facile and tandem approach for the formation of C−O, C−S, and C−Cl bonds. This redox‐neutral protocol can be applied to the synthesis of multisubstituted oxazolidine‐2,4‐diones with good chemoselectivity and good yields of isolated products under mild conditions.

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