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Application of diethyl ethynylphosphonate to the synthesis of 3-phosphonylated beta-lactams via the Kinugasa reaction


Kowalski, Marcin K; Mloston, Grzegorz; Obijalska, Emilia; Heimgartner, Heinz (2017). Application of diethyl ethynylphosphonate to the synthesis of 3-phosphonylated beta-lactams via the Kinugasa reaction. ARKIVOC - Online Journal of Organic Chemistry, (ii):59-67.

Abstract

The easily available diethyl ethynylphosphonate reacts with diverse aldonitrones under Kinugasa reaction conditions at room temperature, providing 3-phosphonylated beta-lactams in good yields. In all cases, the reaction led to the trans-isomer exclusively. The trans-configuration was assigned based on 1H-NMR spectroscopic analysis.

The easily available diethyl ethynylphosphonate reacts with diverse aldonitrones under Kinugasa reaction conditions at room temperature, providing 3-phosphonylated beta-lactams in good yields. In all cases, the reaction led to the trans-isomer exclusively. The trans-configuration was assigned based on 1H-NMR spectroscopic analysis.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2017
Deposited On:24 Jun 2016 12:52
Last Modified:01 Jul 2016 07:02
Publisher:Arkat USA Inc
ISSN:1551-7004
Funders:National Science Center (PL-Cracow), Grant OPUS-7 (UMO-2014/13/B/ST5/04004)
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.3998/ark.5550190.p009.660
Permanent URL: https://doi.org/10.5167/uzh-124661

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