Jump to main content
Jump to site search


Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
03 Feb 2020
Accepted
16 Mar 2020
First published
16 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

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, Advance Article , DOI: 10.1039/D0OB00228C

Social activity

Search articles by author

Spotlight

Advertisements