Enzyme-Like Chemoselective Acylation of Alcohols in the Presence of Amines Catalyzed by a Tetranuclear Zinc Cluster

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 usin...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-03, Vol.130 (10), p.2944-2945
Main Authors: Ohshima, Takashi, Iwasaki, Takanori, Maegawa, Yusuke, Yoshiyama, Asako, Mashima, Kazushi
Format: Article
Language:English
Subjects:
Acylation
Alcohols - chemical synthesis
Alcohols - chemistry
Amides - chemical synthesis
Amides - chemistry
Amines - chemistry
Catalysis
Esters - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Stereoisomerism
Zinc - chemistry
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Summary: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 Zn4(OCOCF3)6O 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja711349r