Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions

Literature Information

Publication Date 2020-03-16
DOI 10.1039/D0OB00228C
Impact Factor 3.876
Authors

Oskar Popik, Barbara Grzeszczyk, Olga Staszewska-Krajewska, Bartłomiej Furman, Marek Chmielewski


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Self-citation Rate: 10.3%
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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