Process for producing optically active...

C - Chemistry – Metallurgy – 07 – C

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C07C 69/675 (2006.01) C07C 67/29 (2006.01) C07C 67/31 (2006.01) C07C 69/78 (2006.01)

Patent

CA 2464446

A process for producing an optically active 3,5-dihydroxyhexanoic acid derivative by stereoselectively reducing an optically active 3-oxo-5- hydroxyhexanoic acid derivative. It necessitates neither an ultralow- temperature reactor nor an incubator and is a simple and economical process in which protection of the 5-position hydroxy is unnecessary. Hydrogen, which is extremely inexpensive, is used as a reducing agent to asymmetrically hydrogenate an optically active 3-oxo-5-hydroxyhexanoic acid derivative by the catalytic action of a ruthenium/optically active phosphine complex, especially an RuBr2BINAP complex prepared from 2,2'-bisdiarylphosphino-1,1'-binaphthyl (BINAP) and a ruthenium complex, to thereby produce an optically active 3,5- dihydroxyhexanoic acid derivative.

L'invention concerne un procédé de production d'un dérivé d'acide 3,5-dihydroxyhexanoïque optiquement actif par réduction stéréosélective d'un dérivé d'acide 3-oxo-5-hydroxyhexanoïque optiquement actif. La mise en oeuvre de ce procédé ne nécessite ni un réacteur à température très basse, ni un incubateur et le procédé est un procédé simple et économique dans lequel une protection de l'hydroxy en position 5 n'est pas nécessaire. L'hydrogène, très peu onéreux, est utilisé comme agent de réduction, aux fins d'hydrogénation asymétrique d'un dérivé d'acide 3-oxo-5-hydroxyhexanoïque optiquement actif par action catalytique d'un complexe de ruthénium/phosphine optiquement active, notamment le complexe RuBr2BINAP préparé à partir de 2,2'bisdiarylphosphino-1-1'-binaphtyle (BINAP) et d'un complexe de ruthénium, permettant ainsi d'obtenir un dérivé d'acide 3,5-dihydroxyhexanoïque optiquement actif.

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