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Agura K, Hayashi Y, Wada M, et al. Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters. Chem Asian J. 2016;11(10):1548-54doi: 10.1002/asia.201600062.
Agura, K., Hayashi, Y., Wada, M., Nakatake, D., Mashima, K., & Ohshima, T. (2016). Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters. Chemistry, an Asian journal, 11(10), 1548-54. https://doi.org/10.1002/asia.201600062
Agura, Kazushi, et al. "Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters." Chemistry, an Asian journal vol. 11,10 (2016): 1548-54. doi: https://doi.org/10.1002/asia.201600062
Agura K, Hayashi Y, Wada M, Nakatake D, Mashima K, Ohshima T. Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters. Chem Asian J. 2016 May 20;11(10):1548-54. doi: 10.1002/asia.201600062. Epub 2016 Apr 14. PMID: 26918549.
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Chem Asian J. 2016 May 20;11(10):1548-54. doi: 10.1002/asia.201600062. Epub 2016 Apr 14.

Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters.

Chemistry, an Asian journal

Kazushi Agura, Yukiko Hayashi, Mari Wada, Daiki Nakatake, Kazushi Mashima, Takashi Ohshima

Affiliations

  1. Graduate School of Pharmaceutical Sciences, Kyushu University, CREST, Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan.
  2. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka, 560-8631, Japan.
  3. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka, 560-8631, Japan. [email protected].
  4. Graduate School of Pharmaceutical Sciences, Kyushu University, CREST, Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan. [email protected].

PMID: 26918549 DOI: 10.1002/asia.201600062

Abstract

The electronic effects of tetranuclear zinc cluster catalysts on transesterification were investigated by changing the carboxylate ligands in the clusters. High catalyst activity crucially depended on the balance between Lewis acidity and Brønsted basicity of the catalyst; this was consistent with the dual activation of both the electrophile and nucleophile by the cooperative zinc centers. In addition, tetranuclear zinc cluster catalysts achieved the transesterification of β-keto esters with unprecedented levels of broad substrate generality, in which a newly developed pentafluoropropionate-bridged zinc cluster and 4-dimethylaminopyridine additive greatly improved the reactivity of sterically congested α- and α,α-disubstituted β-keto esters.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: beta-keto esters; electronic effects; synthesis design; transesterification; zinc

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