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

Min Jin, Congyun Tang, Yingying Li, Shuai Yang, Ying-Tao Yang, Lin Peng, Xiao-Nian Li, Wenjing Zhang (), Zhili Zuo (), Fabien Gagosz and Liang-Liang Wang ()
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Min Jin: Chinese Academy of Sciences
Congyun Tang: Shaoyang University
Yingying Li: Sichuan University of Science & Engineering
Shuai Yang: Chinese Academy of Sciences
Ying-Tao Yang: Chinese Academy of Sciences
Lin Peng: Shaoyang University
Xiao-Nian Li: Chinese Academy of Sciences
Wenjing Zhang: Zhengzhou University
Zhili Zuo: Chinese Academy of Sciences
Fabien Gagosz: University of Ottawa
Liang-Liang Wang: Chinese Academy of Sciences

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Inverse-electron-demand-hetero-Diels-Alder reactions of alkenes with α,β-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 α,β-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 α,β-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.

Date: 2021
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DOI: 10.1038/s41467-021-27521-z

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