Citation
H. Yamamoto et al., Metal ion-mediated diastereoface-selective 1,3-dipolar cycloaddition of nitrile oxides with dipolarophiles bearing an oxazolidinone chiral auxiliary, TETRAHEDR L, 41(17), 2000, pp. 3131-3136
Citations number
44
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039
→ ACNP
Volume
41
Issue
17
Year of publication
2000
Pages
3131 - 3136
Database
ISI
SICI code
0040-4039(20000422)41:17<3131:MID1CO>2.0.ZU;2-Z
Abstract
Magnesium ion-mediated cycloaddition reactions of nitrile oxides to chiral
3-acryroyl-2-oxazolidinones lead to highly diastereoselective formation of
2-isoxazolines. The magnesium ion serves to fix the alpha,beta-unsaturated
moiety through chelation to effect chiral shielding. These asymmetric react
ions provide the first successful examples of Lewis acid-mediated stereocon
trol of nitrile oxide cycloaddition reactions to electron-deficient dipolar
ophiles. (C) 2000 Elsevier Science Ltd. All rights reserved.