Process for producing optically active amino alcohols and intermediates therefore
AssigneeKanto Kaguku Kabushiki Kaisha
InventorsMasahito Watanabe, Kunihiko Murata, Takao Ikariya
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Abstract
A process for producing an optically active amino alcohol is provided that includes a step in which a nitro ketone or a cyano ketone is reacted with a hydrogen-donating organic or inorganic compound in the presence of a transition metal compound catalyst having an optically active nitrogen-containing compound as an asymmetric ligand to give an optically active nitro alcohol or an optically active cyano alcohol, and a step in which the above optically active alcohol is further reduced to efficiently produce an optically active amino alcohol.
Claims11
A process for producing an optically active amino alcohol, comprising:
- a step in which a compound represented by general formula (A)
- wherein R1 is an aromatic monocyclic or aromatic polycyclic hydrocarbon group, which may have one or more substituents, a saturated or unsaturated aliphatic hydrocarbon or alicyclic hydrocarbon group, which may have one or more substituents, or a heteromonocyclic or heteropolycyclic group, which may have one or more substituents,
- R2 and R3 each independently denote a hydrogen atom, a halogen atom, a carboxyl group, a hydroxyl group, an alkoxy group, an aromatic monocyclic or aromatic polycyclic hydrocarbon group, which may have one or more substituents, a saturated or unsaturated aliphatic hydrocarbon or alicyclic hydrocarbon group, which may have one or more substituents and which may contain a heteroatom, or a heteromonocyclic or heteropolycyclic group, which may have one or more substituents, any two of R1 to R3 may bond together so as to form a ring, and X denotes a nitro group or a cyano group, is reacted, in the presence or absence of a base, with an optically active nitrogen-containing compound, a compound of a metal belonging to group VIII of the periodic table, and a hydrogen donor so as to obtain a compound represented by general formula (B)
- wherein R1, R2, R3, and X are as defined above, and * denotes an asymmetric carbon atom, from the compound represented by general formula (A);
- and
- a step in which a compound represented by general formula (C)
- wherein R1, R2, and R3 are as defined above, k denotes an integer of 0 or 1, and * denotes an asymmetric carbon atom, is obtained from the compound represented by general formula (B).
Dependencies are inferred from the claim text.