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
. 2021 Feb 23;60(9):4561-4565.
doi: 10.1002/anie.202013450. Epub 2021 Jan 7.

Copper(I)-Catalyzed Asymmetric Interrupted Kinugasa Reaction: Synthesis of α-Thiofunctional Chiral β-Lactams

Jialin Qi  1 , Fang Wei  1 , Shuai Huang  1 , Chen-Ho Tung  1 , Zhenghu Xu  1   2
Affiliations

Copper(I)-Catalyzed Asymmetric Interrupted Kinugasa Reaction: Synthesis of α-Thiofunctional Chiral β-Lactams

Jialin Qi et al. Angew Chem Int Ed Engl. .

Abstract

A copper(I)-catalyzed asymmetric, three-component interrupted Kinugasa reaction has been developed. Diverse chiral sulfur-containing chiral β-lactams with two consecutive stereogenic centers were synthesized in one step from readily available starting materials in good yields and with excellent diastereo- and enantioselectivity. The key is the interception of in situ formed chiral four membered copper(I) enolate intermediate with sulfur electrophiles.

Keywords: Kinugasa reaction; asymmetric catalysis; copper; sulfur; β-lactams.

PubMed Disclaimer

References

    1. For reviews, see:
    1. I. Ojima, F. Delaloge, Chem. Soc. Rev. 1997, 26, 377;
    1. M. J. Gaunt, C. C. C. Johansson, Chem. Rev. 2007, 107, 5596;
    1. A. Brandi, S. Cicchi, F. M. Cordero, Chem. Rev. 2008, 108, 3988;
    1. C. R. Pitts, T. Lectka, Chem. Rev. 2014, 114, 7930.

LinkOut - more resources