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research article

Improved cis selectivities of carbonyl substituted, stable phosphorus ylides

Patil, Vijay
•
Schlosser, Manfred  
1993
Synlett

Tris(2-methoxymethoxyphenyl)phosphine was readily quaternized when treated with Me bromoacetate. The resulting phosphornium salt was deprotonated to give the corresponding ylide (2-MeOCH2OC6H4)3P+CH-CO2Me (I). I reacted with satd., unsatd., or a-alkoxy substituted aliph. aldehydes to produce a,b-unsatd. esters with moderate to excellent cis-selectivity when methanol was used as the solvent. Thus, I reacted with isobutyraldehyde in MeOH to give a 91:9 mixt. of cis- and trans-Me2CHCH:CHCO2Me. Similarly, aldehyde II gave a 95:5 mixt. of cis- and trans-ester III. [on SciFinder (R)]

  • Details
  • Metrics
Type
research article
DOI
10.1055/s-1993-22372
Author(s)
Patil, Vijay
Schlosser, Manfred  
Date Issued

1993

Published in
Synlett
Issue

2

Start page

125

End page

126

Subjects

Wittig reaction (of tris(methoxymethoxyphenyl)phosphonium ylide with aldehydes in methanol

•

improved cis selectivity in); Ylides Role: SPN (Synthetic preparation)

•

PREP (Preparation) (phosphorus

•

stable

•

tris(methoxymethoxyphenyl)phosphonium

•

prepn. and

•

methoxymethoxyphenylphosphonium ylide prepn Wittig reaction aldehyde; ylide trismethoxymethoxyphenylphosphonium prepn Wittig reaction aldehyde; phosphorus ylide Wittig cis selectivity

Note

CAN 119:27671

23-17

Aliphatic Compounds

Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.

Journal

written in English.

78-84-2 (Isobutyraldehyde); 100-73-2; 123-72-8 (Butanal); 630-19-3 (Pivalaldehyde); 7681-84-7; 10312-83-1; 63493-93-6 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with tris(methoxymethoxyphenyl)phosphonium ylide); 148288-39-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Wittig reaction of, with aldehydes); 148267-90-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with base, ylide by); 1754-62-7P; 13168-99-5P; 13894-63-8P; 13894-64-9P; 19713-73-6P; 20515-15-5P; 20515-16-6P; 20664-51-1P; 25665-54-7P; 27241-17-4P; 27241-18-5P; 57539-96-5P; 75066-86-3P; 75066-87-4P; 122592-49-8P; 122592-63-6P; 132093-58-4P; 148288-40-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 124629-80-7 (Tris(2-methoxymethoxyphenyl)phosphine) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with Me bromoacetate); 96-32-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with tris(methoxymethoxyphenyl)phosphine)

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCO  
Available on Infoscience
March 3, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/226898
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