Reversal of stereoselectivity of Mg(II) catalysed 1,3-dipolar cycloaddition. Acceleration of cycloaddition by microwave irradiation.

Authors
Micuch, P Fisera, L Cyranski, MK Krygowski, TM
Citation
P. Micuch et al., Reversal of stereoselectivity of Mg(II) catalysed 1,3-dipolar cycloaddition. Acceleration of cycloaddition by microwave irradiation., TETRAHEDR L, 40(1), 1999, pp. 167-170
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
1
Year of publication
1999
Pages
167 - 170
Database
ISI
SICI code
0040-4039(19990101)40:1<167:ROSOMC>2.0.ZU;2-Z
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 a Grignard reagent reverses the diastereoselectivity of th e cycloaddition. Microwave irradiation strongly accelerates the reaction wi th only a small effect on its diastereoisomeric excess. (C) 1998 Elsevier S cience Ltd. All rights reserved.