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...

Descripción completa

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
Descripción
Sumario: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.

Ejemplares similares