Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs

Ke-Xin Huang; Ming-Sheng Xie; Dong-Chao Wang; Ji-Wei Sang; Gui-Rong Qu; Hai-Ming Guo

doi:10.1039/C9CC07571B

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Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs†

Ke-Xin Huang,^a Ming-Sheng Xie,

^b Dong-Chao Wang,

^b Ji-Wei Sang,^b Gui-Rong Qu^b and Hai-Ming Guo

*^ab

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* Corresponding authors

^a School of Environment, Henan Normal University, Xinxiang, Henan Province 453007, China
E-mail: ghm@htu.edu.cn

^b Henan Key Laboratory of Organic Functional Molecules and Drugs Innovation, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan Province 453007, China

Abstract

A highly efficient Pd-catalyzed asymmetric formal [3+2] cycloaddition using α-N-heterocyclic acrylates to react with vinyl epoxides has been achieved for the first time to access chiral functionalized tetrahydrofuran skeletons (34 examples, up to 93% yield, >20 : 1 dr and 99% ee). Meanwhile, using a palladium/(S,S)-tBu-FOXAP catalyst or a palladium/(R)-Segphos catalyst, purine or pyrimidine isonucleoside analogs are constructed in high yields and stereoselectivity, respectively. The commercial availability of the catalysts, broad substrate scope and easy transformation of the products make this methodology an attractive method in asymmetric synthesis.

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DOI: https://doi.org/10.1039/C9CC07571B
Article type: Communication
Submitted: 26 Sep 2019
Accepted: 17 Oct 2019
First published: 18 Oct 2019

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Chem. Commun., 2019,55, 13550-13553

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Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs

K. Huang, M. Xie, D. Wang, J. Sang, G. Qu and H. Guo, Chem. Commun., 2019, 55, 13550 DOI: 10.1039/C9CC07571B

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Chemical Communications

Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs†

Abstract

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Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs

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