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

Chem Commun (Camb)

The State Key Laboratory of Chemical Oncogenomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China. and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.

Published: March 2020

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.

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http://dx.doi.org/10.1039/d0cc00061bDOI Listing

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

Chem Commun (Camb)

March 2020

The State Key Laboratory of Chemical Oncogenomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China. and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.

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.

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