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Issue 15, 2020
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Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions

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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


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

Org. Biomol. Chem., 2020,18, 2852-2860
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, 18, 2852
DOI: 10.1039/D0OB00228C

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