Pot‐Economical Synthesis of Fluorinated Pyrrolizinone Derivatives

Abstract A new family of fluorinated dihydropyrrolizinones has been synthesized starting from fluorinated enamino amides and aliphatic conjugated ketones. The reaction comprises a cross metathesis reaction followed by a tandem cycloaromatization/ enamine hydrolysis/ intramolecular Friedel‐Crafts alkylation sequence. This pot‐economical process takes place in good yields (35‐67%), taking into account that it consists of four consecutive reactions. Aromatic enones are also good partners for this protocol although, in this case, the cross metathesis reaction has to be performed in a separated step.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-04-14
DOI
https://doi.org/10.1002/adsc.202500209
Primary Topic
Synthesis of β-Lactam Compounds
Type
article
Field-Weighted Citation Impact
0.00

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article

Pot‐Economical Synthesis of Fluorinated Pyrrolizinone Derivatives

Daniel Gaviña, María Sánchez‐Roselló, Carlos del Pozo, Marcos Escolano et al.
Advanced Synthesis & Catalysis
Synthesis of β-Lactam Compounds
article

Pot‐Economical Synthesis of Fluorinated Pyrrolizinone Derivatives

Daniel Gaviña, María Sánchez‐Roselló, Carlos del Pozo, Marcos Escolano, Santiago Díaz Oltra, Lidia Prieto, Luis Paredes-Soler
article en

Abstract

Abstract A new family of fluorinated dihydropyrrolizinones has been synthesized starting from fluorinated enamino amides and aliphatic conjugated ketones. The reaction comprises a cross metathesis reaction followed by a tandem cycloaromatization/ enamine hydrolysis/ intramolecular Friedel‐Crafts alkylation sequence. This pot‐economical process takes place in good yields (35‐67%), taking into account that it consists of four consecutive reactions. Aromatic enones are also good partners for this protocol although, in this case, the cross metathesis reaction has to be performed in a separated step.

Advanced Synthesis & CatalysisVol. 367(12)
University of Alicante (ES), Universitat de València (ES), Centro de Investigacion Principe Felipe (ES)
Generalitat Valenciana, Ministerio de Ciencia e Innovación, Conselleria de Innovación, Universidades, Ciencia y Sociedad Digital, Generalitat Valenciana
Openalex Percentile: Top 94%
Synthesis of β-Lactam Compounds
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