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Facile synthesis of carbohydrate-integrated isoxazolines through tandem [4+1] cycloaddition and rearrangement of 2-nitroglycals

Authors :
Xue-Wei Liu
Shaohua Xiang
Jing Zeng
Bala Kishan Gorityala
Shuting Cai
Source :
Chemical Communications. 47:8676
Publication Year :
2011
Publisher :
Royal Society of Chemistry (RSC), 2011.

Abstract

Carbohydrate-integrated isoxazolines were synthesized from 2-nitroglycals and sulfur ylides, with the aid of 1-phenylthiourea catalyst. The reactions proceeded via [4+1] annulations and upon subsequent rearrangement, afforded the corresponding isoxazolines in high yields with excellent diastereoselectivities (up to 95% de).

Details

ISSN :
1364548X and 13597345
Volume :
47
Database :
OpenAIRE
Journal :
Chemical Communications
Accession number :
edsair.doi.dedup.....a490edf262ba7625e2c33b5e782dbfc7