Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction

doi:10.1038/s41467-021-27521-z

KIB OpenIR

	Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction
	Jin,Min ; Tang,Congyun ; Li,Yingying ; Yang,Shuai ; Yang,Ying-Tao ; Peng,Lin ; Li,Xiao-Nian ; Zhang,Wenjing ; Zuo,Zhili; Gagosz,Fabien ; Wang,Liang-Liang
	2021
发表期刊	NATURE COMMUNICATIONS
ISSN	2041-1723
卷号	12 期号:1 页码:7188
摘要	Although the hetero-Diels-Alder reaction is a staple of organic chemistry, catalytic asymmetric versions of the inverse-electron demand variant often require specially engineered substrates for the reaction to work. Here the authors cyclize non-activated alkenes with alpha,beta-unsaturated ketones or aldehydes to form chiral fused heterocycles using a chiral phosphoric acid catalyst.Inverse-electron-demand-hetero-Diels-Alder reactions of alkenes with alpha,beta-unsaturated keto compounds allow rapid access to the tetrahydropyran ring found in numerous natural products and bioactive molecules. Despite its synthetic interest, catalytic asymmetric versions of this process remain underdeveloped, especially regarding the use of non-activated alkenes reacting with alpha,beta-unsaturated ketone or aldehyde, for which no report can be found in the literature. Herein, we describe the catalytic inverse-electron-demand-hetero-Diels-Alder reactions between neutral alkenes and an alpha,beta-unsaturated ketones or aldehydes to produce a variety of trans-fused [5,6,8] tricyclic structures containing a central, chiral tetrahydropyran ring. This complex transformation, which is achieved using a chiral phosphoric acid, allows for the formation of four stereogenic centers in a single step with high regio-, diastereo- and enantioselectivity (up to 99% ee). Such level of stereocontrol could be achieved by a key remote double hydrogen atom bonding interaction between the linear substrate and the catalyst.
关键词	DIELS-ALDER REACTION BIOMIMETIC TOTAL-SYNTHESIS ORTHO-QUINONE METHIDES BRONSTED ACID CYCLIZATION ACTIVATION OLEFINS CYCLOADDITIONS CATALYSIS ENTRY
DOI	10.1038/s41467-021-27521-z
WOS记录号	WOS:000729179400036
引用统计	被引频次：7[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/72996
专题	中国科学院昆明植物研究所
作者单位	1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 2.Shaoyang Univ, Sch Food & Chem Engn, Shaoyang 422000, Peoples R China 3.Sichuan Univ Sci & Engn, Sch Chem Engn, Zigong 643000, Peoples R China 4.Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China 5.Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada
推荐引用方式 GB/T 7714	Jin,Min,Tang,Congyun,Li,Yingying,et al. Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction[J]. NATURE COMMUNICATIONS,2021,12(1):7188.
APA	Jin,Min.,Tang,Congyun.,Li,Yingying.,Yang,Shuai.,Yang,Ying-Tao.,...&Wang,Liang-Liang.(2021).Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction.NATURE COMMUNICATIONS,12(1),7188.
MLA	Jin,Min,et al."Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction".NATURE COMMUNICATIONS 12.1(2021):7188.

条目包含的文件		下载所有文件
文件名称/大小	文献类型	版本类型	开放类型	使用许可
140-I02-238-Nature C（2328KB）	期刊论文	出版稿	开放获取	CC BY-NC-SA	浏览下载