Method for asymmetric alkynylation of alpha-imino esters

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

Reexamination Certificate

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C564S305000, C564S393000, C564S487000

Reexamination Certificate

active

07612239

ABSTRACT:
Method for the preparation of asymmetric alkynylated α-amino esters of the formulawherein R1and R2are independently optionally substituted alkyl cycloalkyl, aryl or heteroaryl, and Y is hydrogen or a nitrogen protecting group.

REFERENCES:
Greenspan et al., “Identification of dipeptidyl nitriles as potent and selective inhibitors of cathepsin B through structure-based drug design” J. Med. Chem., vol. 44, No. 26, pp. 4524-4534 (2001).
Ji et al., “Efficient synthesis of beta, gamma-alkynyl alpha-amino acid derivative by Ag(I)-catalyzed alkynylation of alpha-imino esters” Adv. Synth. Catal., vol. 346, pp. 42-44 (2004).
Ji et al., Catalytic asymmetric alkynylation of alpha-imino ester; A versatile approach to optically active unnatural alpha-amino acid derivatives, Proceedings of the National Academy of Sciences of the United States of America, vol. 102, No. 32 (2005).
Taggi et al., “Alpha-imino esters: Versatile substrates for the catalytic, asymmetric synthesis of alpha- and beta-amino acids and beta-lactams”, Acc. Chem., vol. 36, pp. 11-14 (2003).

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