Hypervalent Iodine‐Mediated Alkene Functionalization: Oxazoline and Thiazoline Synthesis via Inter‐/Intramolecular Aminohydroxylation and Thioamination

Hypervalent Iodine‐Mediated Alkene Functionalization: Oxazoline and Thiazoline Synthesis via Inter‐/Intramolecular Aminohydroxylation and Thioamination

A metal‐free oxidative difunctionalization of N‐allylamides and N‐allylthioamides has been developed. This system features the use of a hypervalent iodine oxidant with electron‐deficient amines to access 5‐amino‐oxazoline and thiazoline scaffolds under mild conditions. Notably, various electron‐defi...

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Veröffentlicht in:Advanced synthesis & catalysis 2018-02, Vol.360 (4), p.779-783
Hauptverfasser: Jeon, Hyeonho, Kim, Darong, Lee, Ji Hoon, Song, Jaeyoung, Lee, Won Seok, Kang, Dong Wook, Kang, Soosung, Lee, Seok Beom, Choi, Sungwook, Hong, Ki Bum
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes
Amines
aminohydroxylation
Benzene
hypervalent iodine
Iodine
metal-free
oxazoline
Scaffolds
thiazoline
thioamination
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Beschreibung
Zusammenfassung:A metal‐free oxidative difunctionalization of N‐allylamides and N‐allylthioamides has been developed. This system features the use of a hypervalent iodine oxidant with electron‐deficient amines to access 5‐amino‐oxazoline and thiazoline scaffolds under mild conditions. Notably, various electron‐deficient amines were systematically evaluated and we verified the reaction profile was originated from an attached (benzene)sulfonyl group.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701087