Diastereoselective method of preparing olefins by means of...

Details Diastereoselective method of preparing olefins by means of... Diastereoselective method of preparing olefins by means of...

C - Chemistry, Metallurgy

07

B

C07B 37/04 (2006.01)

Patent

CA 2543880

The invention relates to a diastereoselective method of preparing olefins by means of the Horner-Wadsworth-Emmons reaction consisting in reacting a phosphonate on a carbonyl derivative in the presence of a base in a suitable solvent. According to the invention, the phosphonate has formula A, wherein R¿1? and R¿2? can be identical or different and represent independently a radical having formula (I) in which at least one of the radicals G¿1? or G¿5? represents independently a radical formed by a carbon atom which is in turn linked to three carbon atoms and, preferably, a terbutyl radical, or a phenyl radical which is optionally substituted by one or more radicals that are selected from alkoxy radicals having between 1 and 24 carbon atoms, halogen atoms, heteroatoms such as an oxygen atom, a sulphur atom or a nitrogen atom.

L'invention concerne un procédé diastéréosélectif de préparation d'oléfines par la réaction d'Horner-Wadsworth-Emmons consistant à faire réagir un phosphonate sur un dérivé carbonylé en présence d'une base dans un solvant approprié, le phosphonate étant de formule (A) suivante : Dans laquelle, R1 et R2 sont pris indépendamment et peuvent être identiques ou différents et représentent un radical de formule (I) : dans laquelle au moins un des radicaux G1 ou G5 est pris indépendamment et représente un radical formé par un atome de carbone lui-même relié à trois atomes de carbone, et de préférence un radical terbutyle; ou un radical phényle éventuellement substitué par un ou plusieurs radicaux choisis parmi les radicaaux alkoxy ayant de 1 à 24 atomes de carbone, les atomes d'halogène, ou des hétéroatomes tel qu'un atome d'oxygène, un atome de soufre, ou un atome d'azote.

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