The [2+2] Photocycloaddition of Uracil Derivatives with Ethylene as a General Route to <i>cis</i>-Cyclobutane β-Amino Acids

The first Ficini reaction between ynamides and acrylates is reported herein. The reaction is catalyzed by B(C6F5)3 acting as a Lewis acid and is giving access to stable tri‐substituted aminocyclobutenes in high yield. The resulting products can be hydrogenated and epimerized under basic conditions or in presence of a Lewis acid, providing two distinct trans‐ aminocyclobutane monoester stereoisomers in high yield and diastereoisomeric ratio (up to quantitative yield and >99:1 dr).

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Diastereoselective Synthesis of N‐Heterocycle Substituted Cyclobutanes via Michael Addition onto Cyclobutenes

Robert,

Waser

2024

Chemistry A European J

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Herein, we present a method for the diastereoselective synthesis of N‐heterocycle‐substituted cyclobutanes from commercially available bromocyclobutanes. This method enables the efficient formation of various heterocyclic aminocyclobutane esters and amides using simple reagents. Notably, N‐nucleophiles such as imidazoles, azoles, and nucleobase derivatives were successfully incorporated, enhancing the chemical diversity of small ring building blocks for medicinal chemistry applications.

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The [2+2] Photocycloaddition of Uracil Derivatives with Ethylene as a General Route to cis-Cyclobutane β-Amino Acids

Abstract: A three-step procedure, based on the [2+2]-photochemical reaction of uracils with ethylene followed by controlled degradation of the heterocyclic ring, has been developed for the synthesis of a range of C1-and C2-substituted cis-cyclobutane b-amino acids, in good overall yield.

Cited by 10 publications

References 7 publications

Formation of Alkanes and Arenes by Ring‐forming Reactions

Formation of Alkanes and Arenes by Ring‐forming Reactions

Ficini Reaction with Acrylates for the Stereoselective Synthesis of Aminocyclobutanes

Diastereoselective Synthesis of N‐Heterocycle Substituted Cyclobutanes via Michael Addition onto Cyclobutenes

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