Issue 30, 2011

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

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

Supplementary files

Article information

Article type
Communication
Submitted
21 Apr 2011
Accepted
27 May 2011
First published
29 Jun 2011

Chem. Commun., 2011,47, 8676-8678

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

S. Cai, S. Xiang, J. Zeng, B. K. Gorityala and X. Liu, Chem. Commun., 2011, 47, 8676 DOI: 10.1039/C1CC12327K

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