Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: Regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

Mengchao Tong, Yong Zhang, Cong Qin, Yiwei Fu, Yonghai Liu, Hao Li, Wei Wang

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Alkenylazaarenes as a novel class of dipolarophiles for 1,3-dipolar cycloaddition (1,3-DC) with nitrones was reported. A regioselectivity-switchable synthesis of multisubstituted isoxazolidines had been developed. In the presence of TMSOTf as catalyst, 4-substituted isoxazolidines were obtained as major products with high regio- and diastereoselectivities. Nonetheless, under microwave irradiation in a sealed system with water as solvent, exclusive 5-substituted isoxazolidines were produced in good yields.

Original languageEnglish (US)
Pages (from-to)2945-2949
Number of pages5
JournalOrganic Chemistry Frontiers
Volume5
Issue number20
DOIs
StatePublished - Oct 21 2018
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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