Bridging the final gap in stereocontrolled wittig reactions: methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity

Détails

ID Serval
serval:BIB_17711
Type
Article: article d'un périodique ou d'un magazine.
Collection
Publications
Institution
Titre
Bridging the final gap in stereocontrolled wittig reactions: methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity
Périodique
Chemistry (weinheim An Der Bergstrasse, Germany)
Auteur⸱e⸱s
Wang Q., El Khoury M M., Schlosser M.
ISSN
1521-3765 (Electronic)
ISSN-L
0947-6539
Statut éditorial
Publié
Date de publication
2000
Volume
6
Numéro
3
Pages
420-426
Notes
Publication types: JOURNAL ARTICLE
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.
Pubmed
Création de la notice
19/11/2007 10:39
Dernière modification de la notice
20/08/2019 13:47
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