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Romero E, Minard C, Benchekroun M, et al. Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis. Chemistry. 2017;23(53):12991-12994doi: 10.1002/chem.201702545.
Romero, E., Minard, C., Benchekroun, M., Ventre, S., Retailleau, P., Dodd, R. H., & Cariou, K. (2017). Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis. Chemistry (Weinheim an der Bergstrasse, Germany), 23(53), 12991-12994. https://doi.org/10.1002/chem.201702545
Romero, Eugénie, et al. "Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,53 (2017): 12991-12994. doi: https://doi.org/10.1002/chem.201702545
Romero E, Minard C, Benchekroun M, Ventre S, Retailleau P, Dodd RH, Cariou K. Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis. Chemistry. 2017 Sep 21;23(53):12991-12994. doi: 10.1002/chem.201702545. Epub 2017 Aug 03. PMID: 28627803.
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Chemistry. 2017 Sep 21;23(53):12991-12994. doi: 10.1002/chem.201702545. Epub 2017 Aug 03.

Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis.

Chemistry (Weinheim an der Bergstrasse, Germany)

Eugénie Romero, Corinne Minard, Mohamed Benchekroun, Sandrine Ventre, Pascal Retailleau, Robert H Dodd, Kevin Cariou

Affiliations

  1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198, Gif-sur-Yvette, France.

PMID: 28627803 DOI: 10.1002/chem.201702545

Abstract

Ynamides were used as precursors for the in situ generation of highly reactive ketenimines that could be trapped with imines in a [2+2] cycloaddition. This imino-Staudinger synthesis led to a variety of imino-analogs of β-lactams, namely azetidinimines (20 examples), that could be further functionalized through a broad range of transformations.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Staudinger synthesis; [2+2] cycloaddition; azetidinimines; ketenimines; ynamides

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