Titre
Bridging the final gap in stereocontrolled wittig reactions: methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity
Type
article
Institution
UNIL/CHUV/Unisanté + institutions partenaires
Périodique
Auteur(s)
Wang, Q.
Auteure/Auteur
El Khoury M, M.
Auteure/Auteur
Schlosser, M.
Auteure/Auteur
Liens vers les unités
ISSN
1521-3765
Statut éditorial
Publié
Date de publication
2000
Volume
6
Numéro
3
Première page
420
Dernière page/numéro d’article
426
Notes
Publication types: JOURNAL ARTICLE
Publication Status: ppublish
Publication Status: ppublish
Résumé
After treatment with an appropriate base (butyllithium or sodium amide), 2-alkenyltris(2-methoxymethoxyphenyl)phosphonium salts carrying an allyl, crotyl, or prenyl (3-methyl-2-butenyl) side chain condense with saturated or unsaturated aldehydes to give conjugated dienes with Z/E ratios ranging from 90:10 to > 99:1 and averaging 96:4. Owing to steric congestion, yields are only moderate (on average 41%; extremes 10-79%). The nonvolatile tris(2-methoxymethoxyphenyl)phosphine oxide by-product can be readily isolated and reduced to recover the phosphane starting material, or it may be hydrolyzed to the water-soluble tris(2-hydroxyphenyl)phosphine oxide.
PID Serval
serval:BIB_17711
PMID
Date de création
2007-11-19T08:39:07.215Z
Date de création dans IRIS
2025-05-20T13:19:47Z