Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

Jiru Shao; Caiyun An; Sunewang R. Wang

doi:10.1055/a-1526-7839

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(21): 4030-4041
DOI: 10.1055/a-1526-7839

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Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

Jiru Shao

^aChang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200241, P. R. of China

,

Caiyun An

^aChang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200241, P. R. of China

,

Sunewang R. Wang ∗

^aChang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200241, P. R. of China

^bShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China

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Abstract

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Abstract

A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C–C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

Key words

carbocycles - heterocycles - ring expansion - Brønsted acid - synthetic methods - cyclopropanes - 2-pyrones

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