Organic Chemistry Portal

Abstracts

Search:

Synthesis of 4-Isoxazolines via Visible-Light Photoredox-Catalyzed [3 + 2] Cycloaddition of Oxaziridines with Alkynes

Gwang Seok Jang, Junggeun Lee, Jungseok Seo and Sang Kook Woo*

*Department of Chemistry, University of Ulsan, 93 Daehak-Ro, Nam-Gu, Ulsan 44610, Korea, Email: wooskulsan.ac.kr

G. S. Jang, J. Lee, J. Seo, S. K. Woo, Org. Lett., 2017, 19, 6448-6451.

DOI: 10.1021/acs.orglett.7b03369 (free Supporting Information)


see article for more reactions

Abstract

Visible-light photoredox catalysis enables a green method for [3 + 2] cycloaddition of oxaziridines with alkynes to form 4-isoxazolines in good yields. This atom-economical reaction tolerates various functional groups. Moreover, the cyclization products can be conveniently converted into tetrasubstituted allylic alcohols and enamines.

see article for more examples

proposed mechanism



Key Words

4-isoxazolines


ID: J54-Y2017