Et3B- and Et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions

Authors
Bertrand, MP Coantic, S Feray, L Nouguier, R Perfetti, P
Citation
Mp. Bertrand et al., Et3B- and Et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions, TETRAHEDRON, 56(24), 2000, pp. 3951-3961
Citations number
62
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
24
Year of publication
2000
Pages
3951 - 3961
Database
ISI
SICI code
0040-4020(20000609)56:24<3951:EAERAT>2.0.ZU;2-M
Abstract
1,3-Stereoinduction in the addition of alkyl radicals to glyoxylic imines d erived from various chiral amines has been investigated. New synthetic meth odologies involving Et3B and Et2Zn as mediators have been compared. Dihydro -1,4-oxazin-2-one (2b) gave the highest d.e. but no chemoselectivity. Open chain analogues derived from beta-alkoxyamines led to good stereoinduction when the reaction was performed with Et2Zn which is a bidentate complexing reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.