Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

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...

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Detalles Bibliográficos
Autores principales: Lu, Yuchao, Hou, Chenxi, Ren, Jingli, Xin, Xiaoting, Xu, Hengfu, Pei, Yuxin, Dong, Hai, Pei, Zhichao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274181/
https://www.ncbi.nlm.nih.gov/pubmed/27196888
http://dx.doi.org/10.3390/molecules21050641
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author Lu, Yuchao
Hou, Chenxi
Ren, Jingli
Xin, Xiaoting
Xu, Hengfu
Pei, Yuxin
Dong, Hai
Pei, Zhichao
author_facet Lu, Yuchao
Hou, Chenxi
Ren, Jingli
Xin, Xiaoting
Xu, Hengfu
Pei, Yuxin
Dong, Hai
Pei, Zhichao
author_sort Lu, Yuchao
collection PubMed
description 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.
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spelling pubmed-62741812018-12-28 Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase Lu, Yuchao Hou, Chenxi Ren, Jingli Xin, Xiaoting Xu, Hengfu Pei, Yuxin Dong, Hai Pei, Zhichao Molecules Communication 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. MDPI 2016-05-17 /pmc/articles/PMC6274181/ /pubmed/27196888 http://dx.doi.org/10.3390/molecules21050641 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Lu, Yuchao
Hou, Chenxi
Ren, Jingli
Xin, Xiaoting
Xu, Hengfu
Pei, Yuxin
Dong, Hai
Pei, Zhichao
Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
title Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
title_full Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
title_fullStr Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
title_full_unstemmed Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
title_short Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
title_sort regioselective benzoylation of diols and carbohydrates by catalytic amounts of organobase
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274181/
https://www.ncbi.nlm.nih.gov/pubmed/27196888
http://dx.doi.org/10.3390/molecules21050641
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