Diastereoselection in 1,3-dipolar cycloadditions of a chiral cyclic nitrone to alpha,beta-unsaturated delta-lactones

Authors
Jurczak, M Rabiczko, J Socha, D Chmielewski, M Cardona, F Goti, A Brandi, A
Citation
M. Jurczak et al., Diastereoselection in 1,3-dipolar cycloadditions of a chiral cyclic nitrone to alpha,beta-unsaturated delta-lactones, TETRAHEDR-A, 11(9), 2000, pp. 2015-2022
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
9
Year of publication
2000
Pages
2015 - 2022
Database
ISI
SICI code
0957-4166(20000519)11:9<2015:DI1COA>2.0.ZU;2-Y
Abstract
1,3-Dipolar cycloadditions of the nitrone 1 to alpha,beta-unsaturated delta -lactones: non-chiral 13, racemic mixture 3/4, D-glycero 3, and L-glycero 4 proceed with high stereoselectivity in the cases of 13 and 3 and a signifi cant kinetic resolution in the case of the racemate 3/4. The exo approach t o the re-re sides of the lactones predominates. (C) 2000 Elsevier Science L td. All rights reserved.