Diastereoselective reductive amination process

Details Diastereoselective reductive amination process Diastereoselective reductive amination process

2007-02-27

2007-02-27

Barts, Samuel A (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

11193798

ABSTRACT:
This invention describes a reductive amination process whereby perfluorinated ketones or ketals are combined with α-aminoesters under basic conditions to form metal carboxylates. Diastereoselective reductions of the metal carboxylates enable access to two diastereomers, depending on the reducing conditions.

REFERENCES:
patent: 4535177 (1985-08-01), Golec et al.
Genji Iwasaki, Rieko Kimura, Naganori Numao, and Kiyosi Kondo□□A stereoselective synthesis of N-[(S)-1-Ethoxycarbonyl-3-phenyl propyl]-L-alanine Derivatives by Means of Reductive Amination□□Chemistry Letters pp. 1691-1694,1988.
Barney, CL et al., Tetrahedron Letters, p. 5547-5550 (1990), “A Convenient Synthesis of Hindered Amines and alpha-Trifluoromethylamines from Ketones”.
Ikota, K et al., Chemical and Pharmaceutical Bulletin, p. 887-894 (1983), “Stereochemical Studies LIX. Asymmetric Transamination from (S)-alpha-Amino Acids. Synthesis of (S)-alpha-Amino Acid Esters to Ketones”.
Harada, K et al., Bulletin of Chemical Society of Japan, p. 1367-1370 (1984), “Asymmetric Hydrogenation of Schiff Base Prepared from alpha-Keto Ester with Aliphatic Amino Acid Ester”.
Blacklock, TJ et al., Journal of Organic Chemistry, p. 836-844 (1988), “Synthesis of Semisynthetic Dipeptides Using N-Carboxyanhydrides and Chiral Induction on Raney Nickel. A Method Practical for Large Scale”.

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