The simultaneous in-situ generation of aldehydes and phosphorus ylides: A convenient multi-step one-pot olefination protocol

Citation
Q. Wang et al., The simultaneous in-situ generation of aldehydes and phosphorus ylides: A convenient multi-step one-pot olefination protocol, EUR J ORG C, (12), 1999, pp. 3263-3268
Citations number
38
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434-193X → ACNP
Issue
12
Year of publication
1999
Pages
3263 - 3268
Database
ISI
SICI code
1434-193X(199912):12<3263:TSIGOA>2.0.ZU;2-8
Abstract
The lithium alpha-(dimethylamino)alkoxides resulting from the nucleophilic addition of an organolithium reagent to N,N-dimethylformamide are basic eno ugh to deprotonate alkyltriphenylphosphonium salts suspended in tetrahydrof uran. The aldehydes liberated by the spontaneous decomposition of the resul ting alpha-amino alcohols (hemiaminals) undergo a Wittig reaction with the simultaneously generated phosphorus ylides to afford olefins in excellent o verall yields. This in situ method offers the unique advantage in its appli cability to labile aldehydes which otherwise would become prey to (Z/E)-iso merization or self-condensation processes.