An efficient synthesis of 2-isoxazolines from α-haloketone oximes and dimethyl sulfonium salts. Issue 4 (24th January 2019)

• Record Type: Journal Article
• Authors: Zhao, Sen; Wang, Hang; Sun, Shaofa; Guo, Haibing; Chen, Zhiyu; Wang, Jian; Wang, Lu; Liang, Steven; Wang, Gangqiang
• Is Part Of: Tetrahedron letters. Volume 60:Issue 4(2019)
• Page Start: 382
• Page End: 385
• Publication Date: 2019-01-24
• Subjects: 2-Isoxazoline -- 4, 5-Dihydroisoxazole -- [4+1] Cycloaddition -- α-Haloketone oximes -- Dimethyl sulfonium salt; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.12.062
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 2-Isoxazolines were synthesized efficiently at ambient temperature from a formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides, which were generated in situ from α-haloketone oximes and dimethyl sulfonium salts. This approach provides a new method to synthesize a range of 2-isoxazolines in high yields and high regioselectivity. Highlights: A formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides. Efficient synthesis of 2-isoxazolines. 2-Isoxazolines can be further converted to other well-functionalized building blocks. Abstract: 2-Isoxazolines were synthesized efficiently from a formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides, which were generated in situ from α-haloketone oximes and dimethyl sulfonium salts. This approach provides a new method to synthesize a range of 2-isoxazolines in high yields and high regioselectivity.