Unexpected Formation of 2,2‐Dichloro‐<i>N</i>‐(chloromethyl)acetamides during Attempted Staudinger 2,2‐Dichloro‐β‐lactam Synthesis

Deketelaere, Sari; Broeck, Elias Van Den; Cools, Lore; Deturck, Daan; Naeyaert, Hannes; Hecke, Kristof Van; Stevens, Christian V.; Speybroeck, Véronique Van; D’hooghe, Matthias

doi:10.1002/ejoc.202100975

Eur J Org Chem

2021

DOI: 10.1002/ejoc.202100975

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Unexpected Formation of 2,2‐Dichloro‐N‐(chloromethyl)acetamides during Attempted Staudinger 2,2‐Dichloro‐β‐lactam Synthesis

Sari Deketelaere

Elias Van Den Broeck

Lore Cools

et al.

Abstract: Scheme 1. Reaction mechanism of the Staudinger β-lactam synthesis. Scheme 2. Literature information and preliminary in-house results on Staudinger syntheses involving acid chloride 9 and/or imines 10.

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Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update

Cordero,

Giomi,

Machetti

2024

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The present review is a comprehensive update of the synthesis of monocyclic β-lactams via cycloaddition reactions. According to the IUPAC definition of cycloaddition, both elementary and stepwise processes (formal cycloadditions) have been considered. The years 2019–2022 are covered by the cited literature. The focus of the review is on synthetic aspects with emphasis on the structural scope, reaction conditions, mechanistic aspects, and selectivity results. Selected significant data related to biological activities and synthetic applications are also highlighted.

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Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update

Cordero,

Giomi,

Machetti

2024

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Unexpected Formation of 2,2‐Dichloro‐N‐(chloromethyl)acetamides during Attempted Staudinger 2,2‐Dichloro‐β‐lactam Synthesis

Abstract: Scheme 1. Reaction mechanism of the Staudinger β-lactam synthesis. Scheme 2. Literature information and preliminary in-house results on Staudinger syntheses involving acid chloride 9 and/or imines 10.

Cited by 1 publication

References 34 publications

Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update

Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update

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