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

Hyeonho Jeon, Darong Kim, Ji Hoon Lee, Jaeyoung Song, Won Seok Lee, Dong Wook Kang, Soosung Kang, Seok Beom Lee, Sungwook Choi, Ki Bum Hong

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

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. (Figure presented.).

Original languageEnglish
Pages (from-to)779-783
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number4
DOIs
StatePublished - 15 Feb 2018

Bibliographical note

Funding Information:
This work was supported by the DRC program funded by the National Research Council of Science & Technology (DRC-15-01-KRICT) and Basic Science Research Program through the National Research Foundation of Korea funded by the Ministry of Education, Science and Technology (2015R1D1 A3 A01020384). We thank Dr. Dohyun Moon (POHANG ACCELERATOR LABORATORY) for his help with the X-ray data refinement.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • aminohydroxylation
  • hypervalent iodine
  • metal-free
  • oxazoline
  • thiazoline
  • thioamination

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