Bronsted Acid-Catalyzed Reaction of N-arylnaphthalen-2-amines with Quinone Esters for the Construction of Carbazole and C-N Axially Chiral Carbazole Derivatives

作者全名："Zhang, Mingliang; Zhao, Pin; Wu, Dongqing; Qiu, Zhichao; Zhao, Chenyue; Zhang, Wenyu; Li, Feng; Zhou, Jing; Liu, Lantao"

作者地址："[Zhang, Mingliang; Wu, Dongqing; Qiu, Zhichao; Zhao, Chenyue; Zhang, Wenyu; Li, Feng; Liu, Lantao] Shangqiu Normal Univ, Coll Chem & Chem Engn, Henan Engn Lab Green Synth Pharmaceut, Shangqiu 476000, Henan, Peoples R China; [Zhao, Pin; Liu, Lantao] Zhengzhou Univ, Coll Chem, Zhengzhou 450052, Henan, Peoples R China; [Zhou, Jing] Chongqing Med Univ, Chongqing Res Ctr Pharmaceut Engn, Sch Pharm, Chongqing Key Lab Biochem & Mol Pharmacol, Chongqing 400016, Peoples R China"

通信作者："Wu, DQ; Liu, LT (通讯作者)，Shangqiu Normal Univ, Coll Chem & Chem Engn, Henan Engn Lab Green Synth Pharmaceut, Shangqiu 476000, Henan, Peoples R China.; Liu, LT (通讯作者)，Zhengzhou Univ, Coll Chem, Zhengzhou 450052, Henan, Peoples R China.; Zhou, J (通讯作者)，Chongqing Med Univ, Chongqing Res Ctr Pharmaceut Engn, Sch Pharm, Chongqing Key Lab Biochem & Mol Pharmacol, Chongqing 400016, Peoples R China."

来源：JOURNAL OF ORGANIC CHEMISTRY

ESI学科分类：CHEMISTRY

WOS号：WOS:000935899800001

JCR分区：Q1

影响因子：3.3

年份：2023

卷号：　

期号：　

开始页：　

结束页：　

文献类型：Article; Early Access

关键词：　

摘要："We demonstrated here an efficient synthetic method of carbazole derivatives from readily available N- arylnaphthalen-2-amines and quinone esters catalyzed by Bronsted acid. With this strategy, a series of carbazole derivatives were obtained in good to excellent yields (76 to >99) under mild conditions. Large scale reaction illustrated the synthetic utility of this protocol. Meanwhile, a series of C-N axially chiral carbazole derivatives were also constructed in moderate to good yields (36- 89% yield) with moderate to excellent atroposelectivities (44-94% ee) by using chiral phosphoric acid as a catalyst, which provides a novel strategy for the atroposelective construction of C-N axially chiral compounds and a new member of the C-N atropisomers."

基金机构："National Natural Science Foundation of China [21901152, 21572126]; Key Scientific and Technological Project of Henan Province [202102310003]; Key Science Research of Education Committee in Henan Province [20A150030]; Science and Technology Innovation Talents of Henan Province [2018JQ0011]"

基金资助正文："? ACKNOWLEDGMENTS We are grateful for financial support from the National Natural Science Foundation of China (Nos. 21901152 and 21572126) , the Key Scientific and Technological Project of Henan Province (No. 202102310003) , the Key Science Research of Education Committee in Henan Province (No. 20A150030) , and the Science and Technology Innovation Talents of Henan Province (2018JQ0011) ."