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

Details

Serval ID
serval:BIB_17711
Type
Article: article from journal or magazin.
Collection
Publications
Institution
Title
Bridging the final gap in stereocontrolled wittig reactions: methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity
Journal
Chemistry (weinheim An Der Bergstrasse, Germany)
Author(s)
Wang Q., El Khoury M M., Schlosser M.
ISSN
1521-3765 (Electronic)
ISSN-L
0947-6539
Publication state
Published
Issued date
2000
Volume
6
Number
3
Pages
420-426
Notes
Publication types: JOURNAL ARTICLE
Publication Status: ppublish
Abstract
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
Create date
19/11/2007 10:39
Last modification date
20/08/2019 13:47
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