124629-80-7Relevant academic research and scientific papers
Bridging the final gap in stereocontrolled Wittig reactions: Methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity
Wang, Qian,El Khoury, Mirella,Schlosser, Manfred
, p. 420 - 426 (2000)
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.
Novel ortho-Alkoxy-Substituted Phosphorus Ylides and Their Stereoselectivity in Wittig Reactions
Jeganathan, Suruliappa,Tsukamoto, Masamitsu,Schlosser, Manfred
, p. 109 - 111 (2007/10/02)
The stereochemistry of the reactions between tris(2-methoxymethoxypheny)phosphonioethanide (1f), -butanide (2f), and -phenyl-methanide (3f) and a variety of aldehydes was investigated.Ylides having a β-unbranched aliphatic sidechain, such as 2f, and saturated straight-chain aldehydes give olefins with unprecedented cis-selectivity (cis/trans ca. 200:1).
