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Enzyme-Like Chemoselective Acylation of Alcohols in the Presence of Amines Catalyzed by a Tetranuclear Zinc Cluster
Abstract
Acylation of alcohols and amines is one of the most fundamental reactions. Due to the greater nucleophilicity of the amino group compared to the hydroxyl group, complete N -acylation occurs. Only an enzymatic reaction can promote a highly selective O -acylation reaction, and there are no examples using an artificial catalyst. Here we report that the tetranuclear zinc cluster Zn 4 (OCOCF 3 ) 6 O efficiently catalyzes highly chemoselective O -acylation in the presence of primary and secondary alkyl amines. Our results suggest the high potential of the zinc cluster as the core structure of an artificial enzyme to realize further enzyme-like chemoselective reactions.
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Citations
Cites
Manabe, K., Sun, X.-M., & Kobayashi, S. (2001) · Journal of the American Chemical Society · doi:10.1021/ja016338q · Cited by 215
Cited by
Chang, J., Jin, M., Yao, F., Kim, T. H., Le, V. T., Yue, H., Gunes, F., Li, B., Ghosh, A., Xie, S., et al. (2013) · Advanced Functional Materials · doi:10.1002/adfm201301851 · Cited by 707
Protecting-group-free synthesis as an opportunity for invention
Young, I. S., & Baran, P. S. (2009) · Nature Chemistry · doi:10.1038/nchem.216 · Cited by 667
Enzyme nanoarchitectonics: organization and device application
Ariga, K., Ji, Q., Mori, T., Naito, M., Yamauchi, Y., Abe, H., & Hill, J. P. (2013) · Chemical Society Reviews · doi:10.1039/c2cs35475f · Cited by 397
Chemoselectivity and the Curious Reactivity Preferences of Functional Groups
Afagh, N. A., & Yudin, A. K. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200901317 · Cited by 320
Metadata
- Authors
- Ohshima, T., Iwasaki, T., Maegawa, Y., Yoshiyama, A., & Mashima, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-02-13
- Volume
- 130
- Issue
- 10
- Pages
- 2944-2945
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2075773105
- Cited by
- 180
- References
- 1
- FWCI
- 5.94
- Type
- journal article
- Language
- en
- Open access
- closed
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- Ohshima, T., Iwasaki, T., Maegawa, Y., Yoshiyama, A., & Mashima, K. (2008). Enzyme-Like Chemoselective Acylation of Alcohols in the Presence of Amines Catalyzed by a Tetranuclear Zinc Cluster. Journal of the American Chemical Society. https://doi.org/10.1021/ja711349r
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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