Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1987-11-16
1990-10-09
Gray, Bruce
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562441, 562452, 562456, 562457, 562466, 562468, 562478, 562465, 562490, 562491, 562496, 562598, 562606, C07C22942
Patent
active
049622307
ABSTRACT:
A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,
is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.
According to the process of the invention, the desired optically active carboxylic acids which can be widely used as raw materials for synthesizing various useful compounds, for example, as intermediates for synthesizing physiologically active substances of natural materials and also as liquid crystal materials can be industrially advantageously produced.
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The Chemical Society of Japan, Bull. Chem Soc. Jpn. 55, 2917-2921 (1982), "Synthesis of Sugar Derivatives of Tervalent Phosphorus Compounds and Their Application to Homogeneous Assymetric Hydrogenation," Yamashita, et al.
"Synthesis of Novel Chiral Ruthenium Complexes of 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl and Their use as Asymmetric Catalysts", Journal Chem. Soc. Commun., 1985, I. Ikrariya, et al.
Akutagawa Susumu
Kumobayashi Hidenori
Noyori Ryoji
Ohta Tetsuo
Sayo Noboru
Gray Bruce
Takasago International Corporation
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