Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Comparative Study
. 2005 Aug 9;102(32):11196-200.
doi: 10.1073/pnas.0502105102. Epub 2005 Aug 1.

Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives

Jian-Xin Ji  1 , Jing Wu, Albert S C Chan
Affiliations
Comparative Study

Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives

Jian-Xin Ji et al. Proc Natl Acad Sci U S A. .

Abstract

The catalytic asymmetric introduction of alkynyl functionality to alpha-amino acid derivatives was realized by the direct addition of terminal alkynes to alpha-imino ester in the presence of chiral Cu(I) complex under mild reaction conditions. Owing to the rich chemistry to which alkyne can be subjected, the present system provides a remarkably versatile tool for the construction of optically active alpha-amino acid derivatives. Good yields and enantiomeric excess values were achieved with an array of terminal alkynes and challenging, biologically active, unnatural alpha-amino acid derivatives could be conveniently obtained.

PubMed Disclaimer

Figures

Scheme 1.
Scheme 1.
Ag(I)-catalyzed alkynylation of α-imino ester.
Fig. 1.
Fig. 1.
Chiral ligands for screen.
Scheme 2.
Scheme 2.
Modification of compound 3b.
Scheme 3.
Scheme 3.
Proposed mechanism for the alkynylation of α-imino ester.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Barrett, G. C. (1985) Chemistry and Biochemistry of the Amino Acids (Chapman & Hall, London).
    1. Williams, R. M. (1989) Synthesis of Optically Active α-Amino Acids (Pergamon, Oxford).
    1. Duthaler, R. O. (1994) Tetrahedron 50, 1539–1650.
    1. Hegedus, L. S. (1995) Acc. Chem. Res. 28, 299–305.
    1. Chin, J. W., Cropp, T. A., Anderson, J. C., Mukherji, M., Zhang, Z. & Schultz, P. G. (2003) Science 301, 964–967. - PubMed

Publication types

LinkOut - more resources