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Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

Tetsuji Yata, Yuji Kita, Yoshihiro Nishimoto* and Makoto Yasuda*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: nishimotochem.eng.osaka-u.ac.jp, yasudachem.eng.osaka-u.ac.jp

T. Yata, Y. Kita, Y. Nishimoto, M. Yasuda, J. Org. Chem., 2019, 84, 14330-14341.

DOI: 10.1021/acs.joc.9b02186 (free Supporting Information)


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Abstract

The oxyindation of carbonyl-ene-yne compounds with indium trihalides provides di-, tri-, and tetrasubstituted 2-pyrones bearing a carbon-indium bond. The metalated 2-pyrones can be oxidized or cross-coupled to multifunctionalized 2-pyrones.

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Key Words

2-pyrones, PIDA


ID: J42-Y2019