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Facile synthesis of carbohydrate-integrated isoxazolines through tandem [4+1] cycloaddition and rearrangement of 2-nitroglycals†
Shuting Cai,Shaohua Xiang,Jing Zeng,Bala Kishan Gorityala,Xue-Wei Liu
Chemical Communications Pub Date : 06/29/2011 00:00:00 , DOI:10.1039/C1CC12327K
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).

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