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Molecules 2016, 21(5), 641;

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A & F University, Yangling 712100, China
School of Chemistry & Chemical Engineering, Huazhong University of Science & Technology, Luoyu Road 1037, Wuhan 430074, China
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 23 March 2016 / Revised: 21 April 2016 / Accepted: 10 May 2016 / Published: 17 May 2016
(This article belongs to the Section Bioorganic Chemistry)
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A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy. View Full-Text
Keywords: benzoylation; regioselectivity; DBU; benzoylimidazole; catalysis benzoylation; regioselectivity; DBU; benzoylimidazole; catalysis

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Lu, Y.; Hou, C.; Ren, J.; Xin, X.; Xu, H.; Pei, Y.; Dong, H.; Pei, Z. Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase. Molecules 2016, 21, 641.

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