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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.

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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

References

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