Issue 15, 2020
From the journal:

Organic & Biomolecular Chemistry

Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions†

Oskar Popik,a   Barbara Grzeszczyk, ORCID logo a   Olga Staszewska-Krajewska, ORCID logo a   Bartłomiej Furman ORCID logo a  and  Marek Chmielewski ORCID logo *a  

* Corresponding authors

a Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
E-mail: marek.chmielewski@icho.edu.pl

Abstract

Intramolecular Kinugasa reactions on in situ generated carbohydrate-derived alkynylnitrones are described. The effects of the length of chains, their mutual configuration, influence of experimental conditions on product distribution and feasibility of the β-lactam ring construction were studied. Intramolecular reactions proceed with high stereoselectivity to provide in each case one product only. The cycloadducts from tartaric acid were converted into the corresponding non-racemic 4-acetoxy azetidinones in good yields.

Graphical abstract: Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions

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Article information

DOI
https://doi.org/10.1039/D0OB00228C
Article type
Paper
Submitted
03 Feb 2020
Accepted
16 Mar 2020
First published
16 Mar 2020

Org. Biomol. Chem., 2020,18, 2852-2860

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Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions

O. Popik, B. Grzeszczyk, O. Staszewska-Krajewska, B. Furman and M. Chmielewski, Org. Biomol. Chem., 2020, 18, 2852 DOI: 10.1039/D0OB00228C

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