Regioselective and Enantioselective Synthesis of beta-Indolyl Cyclopentenamides by Chiral Anion Catalysis

doi:10.1002/anie.201807010

	Regioselective and Enantioselective Synthesis of beta-Indolyl Cyclopentenamides by Chiral Anion Catalysis
	Rajkumar, Subramani1 ; Wang, Jiawen1 ; Zheng, Sujuan 2; Wang, Donglei1 ; Ye, Xueqian1 ; Li, Xuejiao1 ; Peng, Qian 2; Yang, Xiaoyu1
	2018-10-08
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year])
ISSN	1433-7851
卷号	57 期号:41 页码:13489-13494
发表状态	已发表
DOI	10.1002/anie.201807010
摘要	The regioselective and enantioselective synthesis of beta-indolyl cyclopentenamides, a versatile chiral building block, by asymmetric addition of indoles to alpha,beta-unsaturated iminium intermediates has been achieved through chiral anion catalysis. Key to the success of this methodology is the generation of a chiral anion-paired ketone-type alpha,beta-unsaturated iminium intermediate from alpha-hydroxy enamides. Preliminary mechanistic studies and DFT calculations are consistent with a mechanism involving multiple, concurrent pathways for isomerization of the initially formed azaallylcation into the key alpha,beta-unsaturated iminium intermediate, all mediated by the phosphoric acid catalyst.
关键词	chiral anion catalysis organocatalysis indoles reaction mechanisms synthetic methods
收录类别	SCI ; SCIE ; EI ; IC ; CCR
语种	英语
资助项目	NSF of Tianjin Municipality[18JCYBJC21400]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000446306600018
出版者	WILEY-V C H VERLAG GMBH
WOS关键词	COUNTERANION-DIRECTED CATALYSIS ; VERSATILE BUILDING-BLOCKS ; BRONSTED ACID ; CYCLIC ENONES ; ALPHA,BETA-UNSATURATED KETONES ; ASYMMETRIC FUNCTIONALIZATION ; ELECTROPHILIC ACTIVATION ; IMINIUM ACTIVATION ; MICHAEL ADDITION ; PHOSPHORIC-ACIDS
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/28076
专题	物质科学与技术学院_PI研究组_杨晓瑜组物质科学与技术学院_硕士生物质科学与技术学院_本科生物质科学与技术学院_博士生
通讯作者	Peng, Qian; Yang, Xiaoyu
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China 2.Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
第一作者单位	物质科学与技术学院
通讯作者单位	物质科学与技术学院
第一作者的第一单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Rajkumar, Subramani,Wang, Jiawen,Zheng, Sujuan,et al. Regioselective and Enantioselective Synthesis of beta-Indolyl Cyclopentenamides by Chiral Anion Catalysis[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2018,57(41):13489-13494.
APA	Rajkumar, Subramani.,Wang, Jiawen.,Zheng, Sujuan.,Wang, Donglei.,Ye, Xueqian.,...&Yang, Xiaoyu.(2018).Regioselective and Enantioselective Synthesis of beta-Indolyl Cyclopentenamides by Chiral Anion Catalysis.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,57(41),13489-13494.
MLA	Rajkumar, Subramani,et al."Regioselective and Enantioselective Synthesis of beta-Indolyl Cyclopentenamides by Chiral Anion Catalysis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57.41(2018):13489-13494.