A general method for the vinylation of nitrones. Synthesis of allyl hydroxylamines and allyl amines

Authors
Merino, P Anoro, S Franco, S Gascon, JM Martin, V Merchan, FL Revuelta, J Tejero, T Tunon, V
Citation
P. Merino et al., A general method for the vinylation of nitrones. Synthesis of allyl hydroxylamines and allyl amines, SYN COMMUN, 30(16), 2000, pp. 2989-3021
Citations number
79
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
16
Year of publication
2000
Pages
2989 - 3021
Database
ISI
SICI code
0039-7911(2000)30:16<2989:AGMFTV>2.0.ZU;2-7
Abstract
An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exce ption of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable a llyl amines.