Enantioselective access to tricyclic tetrahydropyran derivatives by a remote hydrogen bonding mediated intramolecular IEDHDA reaction
文献类型：期刊论文
| 作者 | Jin,Min; Tang,Congyun; Li,Yingying; Yang,Shuai; Yang,Ying-Tao; Peng,Lin; Li,Xiao-Nian; Zhang,Wenjing; Zuo,Zhili ; Gagosz,Fabien
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| 刊名 | NATURE COMMUNICATIONS
 |
| 出版日期 | 2021 |
| 卷号 | 12期号:1页码:7188 |
| ISSN号 | 2041-1723 |
| 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 |
| 英文摘要 | 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. |
| WOS记录号 | WOS:000729179400036 |
| 源URL | [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.Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 3.Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada 4.Sichuan Univ Sci & Engn, Sch Chem Engn, Zigong 643000, Peoples R China 5.Shaoyang Univ, Sch Food & Chem Engn, Shaoyang 422000, Peoples R China |
| 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. |
入库方式： OAI收割
来源：昆明植物研究所
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