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Easy Access to Esters with a Benzylic Quaternary Carbon Center from Diallyl Malonates by Palladium-Catalyzed Decarboxylative Allylation

Daisuke Imao, Akihiro Itoi, Asako Yamazaki, Masamichi Shirakura, Ryota Ohtoshi, Kenta Ogata, Yohki Ohmori, Tetsuo Ohta* and Yoshihiko Ito

*Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan, Email: totamail.doshisha.ac.jp

D. Imao, A. Itoi, A. Yamazaki, M. Shirakura, R. Ohtoshi, K. Ogata, Y. Ohmori, T. Ohta, Y. Ito, J. Org. Chem., 2007, 72, 1534-1537.

DOI: 10.1021/jo0621569 (free Supporting Information)


Abstract

Diallyl 2-alkyl-2-arylmalonates underwent palladium-catalyzed decarboxylative allylation quickly under mild conditions. In contrast, no reaction took place with diallyl 2,2-dialkylmalonates under the same conditions. Electron-donating phosphine ligands were found to be vital for this reaction.

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Key Words

Esters, Tsuji-Trost Reaction


ID: J42-Y2007-0720