1,3-dipolar cycloaddition of chirally modified vinylboronic ester with nitrile oxides

Authors
Zhang, A Kan, Y Zhao, GL Jiang, B
Citation
A. Zhang et al., 1,3-dipolar cycloaddition of chirally modified vinylboronic ester with nitrile oxides, TETRAHEDRON, 56(7), 2000, pp. 965-970
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
7
Year of publication
2000
Pages
965 - 970
Database
ISI
SICI code
0040-4020(20000211)56:7<965:1COCMV>2.0.ZU;2-I
Abstract
Chiral modified vinylboronic ester 1, derived from D-(+)-mannitol, reacted with nitrile oxides to afford optically active isoxazolines. The regioselec tivity was excellent and moderate stereoselectivity (up to 60% d.e.) was ac hieved. The configuration of new chiral centres in all the isoxazoline prod ucts was established by NMR: analysis or X-ray analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.