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Hypervalent Iodine‐Mediated Alkene Functionalization: Oxazoline and Thiazoline Synthesis via Inter‐/Intramolecular Aminohydroxylation and Thioamination
Author(s) -
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
Publication year - 2018
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.201701087
Subject(s) - hypervalent molecule , chemistry , thiazoline , oxazoline , intramolecular force , alkene , sulfonyl , racemization , surface modification , iodine , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl
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.