Synthesis of β‐N‐Heterocyclic‐Cyclobutane‐Fused Bicyclic γ‐Lactones from 2‐Hydroxycyclobutanone and Carboxamide‐Bearing Wittig Reagents

A cascade reaction has been established that enables access to structurally diverse 2‐oxabicyclo[3.2.0]heptan‐3‐ones bearing a benzo[ d ]oxazol‐2(3H)‐one moiety at the bridgehead quaternary center in moderate to good yields in a single operation. The reaction illustrates the potential of 2‐hydroxycyclobutanone as a substrate for the rapid preparation of unusual and complex molecular frameworks.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-05-26
DOI
https://doi.org/10.1002/ejoc.202500332
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
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article

Synthesis of β‐N‐Heterocyclic‐Cyclobutane‐Fused Bicyclic γ‐Lactones from 2‐Hydroxycyclobutanone and Carboxamide‐Bearing Wittig Reagents

Angelo Frongia, V. Frau, David J. Aitken, Stefano Barranco et al.
European Journal of Organic Chemistry
Synthetic Organic Chemistry Methods
article

Synthesis of β‐N‐Heterocyclic‐Cyclobutane‐Fused Bicyclic γ‐Lactones from 2‐Hydroxycyclobutanone and Carboxamide‐Bearing Wittig Reagents

Angelo Frongia, V. Frau, David J. Aitken, Stefano Barranco, Régis Guillot, Pierluigi Caboni, Mauro Uras
article en

Abstract

A cascade reaction has been established that enables access to structurally diverse 2‐oxabicyclo[3.2.0]heptan‐3‐ones bearing a benzo[ d ]oxazol‐2(3H)‐one moiety at the bridgehead quaternary center in moderate to good yields in a single operation. The reaction illustrates the potential of 2‐hydroxycyclobutanone as a substrate for the rapid preparation of unusual and complex molecular frameworks.

European Journal of Organic ChemistryVol. 28(26)
Centre National de la Recherche Scientifique (FR), University of Cagliari (IT), Université Paris-Saclay (FR), Institut des Sciences des Plantes de Paris Saclay (FR), Institut des Sciences Moléculaires d'Orsay (FR), Istituto Nazionale di Fisica Nucleare, Sezione di Cagliari (IT), Institut de Chimie Moléculaire et des Matériaux d'Orsay (FR)
Clean water and sanitation
Openalex Percentile: Top 91%
Synthetic Organic Chemistry Methods
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Synthesis of β‐N‐Heterocyclic‐Cyclobutane‐Fused Bicyclic γ‐Lactones from 2‐Hydroxycyclobutanone and Carboxamide‐Bearing Wittig Reagents — Angelo Frongia, V. Frau, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS