Process for the preparation of chiral beta amino acid...

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

Reexamination Certificate

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C564S337000, C548S262400

Reexamination Certificate

active

07468459

ABSTRACT:
The present invention relates to a process for the efficient preparation of enantiomerically enriched beta amino acid derivatives which are useful in the asymmetric synthesis of biologically active molecules. The process comprises an enantioselective hydrogenation of a prochiral beta amino acrylic acid derivative substrate in the presence of a transition metal precursor complexed with a chiral ferrocenyl diphosphine ligand.

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Zhu, et al., “Highly efficient Asymmetric Synthesis of β-Amino Acid Derivatives via Rhodium-Catalyzed Hydrogenation of β-(Acylamino)acrylates”,J. Org. Chem, vol. 64, pp. 6907-6910 (1999).
Lubell, et al., “Enantioselective Synthesis of β-Amino Acids based in BINAP-Ruthenium(II) Catalyzed Hydrogenation”,Tetrahedron Asymmetry, vol. 2, No. 7, pp. 543-554 (1991).
Hsiao, et al., “Highly Efficient Synthesis of β-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected Enamines”,J. Am. Chem. Soc., vol. 126, pp. 9918-9919 (2004).
Hayashi, et al. “Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition Metal Complexes. I. Preparation of Chiral Ferrocenylphosphines”,Bull. Chem. Soc. Jpn., vol. 53, pp. 1138-1151 (1980).

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