Process for producing optically active amide from α β- unsaturated amide derivative in the presence of transition metal complex containing phosphine-phosphorane compound and transition metal
AssigneeTakasago International Corporation
InventorsKazuhiko Matsumura, Takao Saito
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Abstract
A novel process for producing an optically active amide excellent in chemical selectivity and enantioselectivity by asymmetric hydrogenation of an α,β-unsaturated amide and also allowing the reaction to proceed efficiently even when a trace amount of a catalyst is used relative to the substrate as compared with the amount in a conventional process. An optically active amide is produced by asymmetric hydrogenation of an α,β-unsaturated amide derivative in the presence of a transition metal complex containing a specific phosphine-phosphorane compound.
Claims6
A process for producing an optically active amide comprising a step of asymmetric hydrogenation of an α,β-unsaturated amide derivative in the presence of a transition metal complex containing a phosphine-phosphorane compound represented by the following general formula (21) and a transition metal selected from the group consisting of Ir, Rh, Ru, Pd, and Ni.
- (wherein R11 and R21 are the same or different, and each represents a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkyl group having 1 to 6 carbon atoms which has at least one substituent (an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom), a cycloalkyl group having 3 to 7 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a ring-substituted aralkyl group, a phenyl group, a phenyl group having at least one substituent (an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms which is substituted by at least one halogen atom, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom, an amino group, an amino group substituted by an alkyl group, 3,4-methylenedioxy group, 3,4-ethylenedioxy group, or 3,4-propylenedioxy group), a five-membered heteroaromatic ring residual group, a naphthyl group, or a naphthyl group having substituent(s) (an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom);
- R31, R41, R51, and R61 are the same or different, and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, and each of R31 and R41, R41 and R51, and R51 and R61 may be together combined to form a ring containing at least one heteroatom;
- and R71 and R81 are the same or different, and each represents hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a perfluoroalkyl group, a phenyl group, a phenyl group having at least one substituent (an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms which is substituted by halogen atom(s), an alkoxy group having 1 to 6 carbon atoms, or a halogen atom), an aralkyl group having 7 to 12 carbon atoms, or a ring-substituted aralkyl group).
Dependencies are inferred from the claim text.