Process for hydrogenating unactivated imines using ruthenium...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S489000

Reexamination Certificate

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10513321

ABSTRACT:
A process is provided for the hydrogenation or asymmetric hydrogenation of dialkyl, alkylalkenyl and dialkenyl imines of formula (II) to provide amines of formula (III), wherein, (i) R1and R2are optionally substituted cyclic, linear or branched alkyl or alkenyl; R3is a hydrogen atom, a hydroxy radical, optionally substituted C1to C8cyclic, linear or branched alkyl or alkenyl, optionally substituted aryl; or (ii) R1is alkyl or alkenyl, R2is alkyl or alkenyl and the two are linked together or with R3to form one or more rings; using a catalytic system comprising a base and a ruthenium complex containing (1) a diamine and (2) a diphosphine ligand or monodentate phosphine ligands in hydrogenation and asymmetric hydrogenation processes

REFERENCES:
patent: WO02/08169 (2002-01-01), None
Abdur-Rashid et al., Organometallics (2001), 20, p. 1047-1049.
Abdur-Rashid, K. et al., “RuHCl(diphosphine)(diamine): Catalyst Precursors for the Steroselective Hydrogenation of Ketones and Imines”, Organometallics, 2001, pp. 1047-1049, vol. 20.
Cobley, C. J. et al., “Enantioselective Hydrogenation of Imines using a Diverse Library of Ruthenium Dichloride (diphosphine) (diamine) Precatalysts”, Advanced Synthesis and Catalysis, 2003, pp. 195-201, vol. 345.
Henschke, J. P. et al., “Synthesis and Application of HexaPHEMP, a Novel Biaryl DiPhosphine Ligand”, Advanced Synthesis and Catalysis, 2003, pp. 300-307, vol. 345.
Cobley, C. J. et al., “The synthesis of S 18986, a chiral AMPA receptor modulator, via catalytic asymmetric hydrogenation”, Tetrahedron: Asymmetry, 2003, pp. 3431-3433, vol. 14.

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