Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines

doi:10.1002/anie.201913896

	Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines
	Rajkumar, Subramani1 ; Tang, Mengyao1,2 ; Yang, Xiaoyu1
	2019-12-27
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year])
ISSN	1433-7851
EISSN	1521-3773
发表状态	已发表
DOI	10.1002/anie.201913896
摘要	An efficient method for the asymmetric synthesis of 4H-3,1-benzoxazines was developed by kinetic resolution of 2-amido benzyl alcohols using chiral phosphoric acid catalyzed intramolecular cyclizations. A broad range of benzyl alcohols (both secondary and tertiary alcohols) were kinetically resolved with high selectivities, with an s factor of up to 94. Mechanistic studies were performed to elucidate the mechanism of these reactions, wherein the amide moieties reacted as the electrophiles. Gram-scale reaction and facile transformations of the chiral products demonstrate the potential of this method in asymmetric synthesis of biologically active chiral heterocycles.
关键词	alcohols heterocycles kinetic resolution organocatalysis reaction mechanisms
收录类别	SCI ; SCIE ; EI ; IC ; CCR
资助项目	NSFC[21702138]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000504483000001
出版者	WILEY-V C H VERLAG GMBH
WOS关键词	BRONSTED ACID ; ENANTIOSELECTIVE SYNTHESIS ; TERTIARY ALCOHOLS ; HYDROXY ESTERS ; POTENT ; CHLOROCYCLIZATION ; CYCLOADDITION ; CONSTRUCTION ; INHIBITORS ; ALKYLATION
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/104974
专题	物质科学与技术学院_硕士生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_博士生
共同第一作者	Tang, Mengyao
通讯作者	Yang, Xiaoyu
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, 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,Tang, Mengyao,Yang, Xiaoyu. Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019.
APA	Rajkumar, Subramani,Tang, Mengyao,&Yang, Xiaoyu.(2019).Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA	Rajkumar, Subramani,et al."Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2-Amido Benzyl Alcohols: Asymmetric Synthesis of 4H-3,1-Benzoxazines".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019).