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Synthesis of cyclobutane-fused oxygen-containing tricyclic framework via thermally promoted intramolecular cycloaddition of cyclohexadienone-tethered allenes

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Abstract

We have developed a unique approach for the thermally promoted cycloaddition of cyclohexadienone-tethered allenes to form a versatile cyclobutane-fused oxygen-containing tricyclic framework in an environmentally friendly and atomic economic fashion with high regioselectivity. The reaction encompasses a broad substrate scope and functional group tolerance of cyclohexadienone moieties. Moreover, the cycloaddition was also applicable to the late-stage functionalization of pharmaceutically relevant compounds.

Graphical abstract: Synthesis of cyclobutane-fused oxygen-containing tricyclic framework via thermally promoted intramolecular cycloaddition of cyclohexadienone-tethered allenes

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Article information


Submitted
03 Jan 2020
Accepted
11 Feb 2020
First published
12 Feb 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Synthesis of cyclobutane-fused oxygen-containing tricyclic framework via thermally promoted intramolecular cycloaddition of cyclohexadienone-tethered allenes

S. Zhai, S. Qiu, L. Chen, Y. Niu, Y. Yu, B. Yang, B. Zhang, C. Han, L. Yang and H. Zhai, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00061B

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