Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions-Reference-Cited by-同舟云学术

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Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions

Published:2020 Issue:15 Volume:18 Page:2852-2860
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Popik Oskar¹²³,Grzeszczyk Barbara¹²³^ORCID,Staszewska-Krajewska Olga¹²³^ORCID,Furman Bartłomiej¹²³^ORCID,Chmielewski Marek¹²³^ORCID

Affiliation:

1. Institute of Organic Chemistry of the Polish Academy of Sciences

2. 01-224 Warsaw

3. Poland

Abstract

Intramolecular Kinugasa reactions on in situ generated carbohydrate-derived alkynylnitrones are described. Subsequent transformations of cycloadducts followed by epimerization at the C-4 carbon atom led to trans-substituted azetidinones with high stereoselectivity.

Funder

Narodowe Centrum Nauki

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/D0OB00228C

Reference29 articles.

1. The reactions of copper(I) phenylacetylide with nitrones

2. β-Lactam Synthesis by the Kinugasa Reaction

3. Kinugasa reaction: an ‘ugly duckling’ of β-lactam chemistry

4. Novel Syntheses of Azetidines and Azetidinones

5. Chemical Synthesis of β-Lactams: Asymmetric Catalysis and Other Recent Advances

Cited by 7 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update;Reactions;2024-08-16

2. The Kinugasa Reaction;Organic Reactions;2024-03-22

3. Stereoselective [2+2] Cycloadditions: Synthesis of a Tri-O-Bn-D-Glucal-derived β-Lactam;Organic Syntheses;2022

4. Synthesis of N-sulfonated azetidines and β-lactemes and their applications;N-Sulfonated-N-Heterocycles;2022

5. Metal-Catalyzed Synthesis of β-Lactam Antibiotics;Alternatives to Antibiotics;2022

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