title: Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase.
abstract: 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.
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. luyuchao_2006@126.com.
authors.forename: Yuchao
authors.initials: Y
authors.lastname: Lu
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. houchenxi2015@126.com.
authors.forename: Chenxi
authors.initials: C
authors.lastname: Hou
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. renjingli12345@163.com.
authors.forename: Jingli
authors.initials: J
authors.lastname: Ren
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. 18700814753@163.com.
authors.forename: Xiaoting
authors.initials: X
authors.lastname: Xin
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. xhf130@126.com.
authors.forename: Hengfu
authors.initials: H
authors.lastname: Xu
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. peiyx@nwafu.edu.cn.
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Pei
authors.affiliation: School of Chemistry &amp; Chemical Engineering, Huazhong University of Science &amp; Technology, Luoyu Road 1037, Wuhan 430074, China. hdong@mail.hust.edu.cn.
authors.forename: Hai
authors.initials: H
authors.lastname: Dong
authors.affiliation: Shaanxi Key Laboratory of Natural Products &amp; Chemical Biology, College of Science, Northwest A &amp; F University, Yangling 712100, China. peizc@nwafu.edu.cn.
authors.forename: Zhichao
authors.initials: Z
authors.lastname: Pei
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004101:Dihydroxydihydrobenzopyrenes / Q000138:chemical synthesis / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D004101:Dihydroxydihydrobenzopyrenes; D007093:Imidazoles; C029899:imidazole; D014508:Urea; C483182:N,N'-dibutylurea
keywords: DBU; benzoylation; benzoylimidazole; catalysis; regioselectivity