Reversal of diastereoselectivity of nitrile oxide 1,3-dipolar cycloadditions by Mg(II). Acceleration of cycloaddition by microwave irradiation

Authors
Micuch, P Fisera, L Cyranski, MK Krygowski, TM Krajcik, J
Citation
P. Micuch et al., Reversal of diastereoselectivity of nitrile oxide 1,3-dipolar cycloadditions by Mg(II). Acceleration of cycloaddition by microwave irradiation, TETRAHEDRON, 56(30), 2000, pp. 5465-5472
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
30
Year of publication
2000
Pages
5465 - 5472
Database
ISI
SICI code
0040-4020(20000721)56:30<5465:RODONO>2.0.ZU;2-1
Abstract
1,3-Dipolar cycloadditions of mesitonitrile oxide to Baylis-Hillman adducts (beta-hydroxy-alpha-methylene esters) proceed regioselectively in good yie lds. Addition of Grignard reagent reverses the diastereoselectivity of the cycloaddition. Microwave irradiation strongly accelerates the reaction with only a small effect on its diastereoisomeric excess. (C) 2000 Elsevier Sci ence Ltd. All rights reserved.