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Enantioselective synthesis of tetrasubstituted allenes via addition/arylation tandem reaction of 2-activated 1,3-enynes

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Abstract

We report the development of a new class of multifunctional chiral guanidine/Pd(0) catalyst system for 1,4-addition/arylation tandem reaction. A variety of tetra-substituted allenes were readily accessible from three-component “one-pot” transformations of acyclic or cyclic 2-activated 1,3-enynes, malonates and halobenzenes under mild reaction conditions. High levels of yield and enantioselectivity were achieved in the construction of stereogenic center and axis using readily available acyclic guanidine-amides. The mechanistic studies suggest that the guanidine/Pd(0) collaboration has obvious synergism to both base-dominated conjugate addition, and Pd(0)-dominated Heck-type reaction.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21625205) and the Sichuan University (2020SCUNL204). We thank for Dr. Bo Gao (Sichuan University) for the help with the mass spectrometry and Dr. Yuqiao Zhou (Sichuan University) for the assistance with X-ray analyses.

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Authors and Affiliations

  1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China

    Yongyan Zhang, Jin Wu, Lichao Ning, Qianping Chen, Xiaoming Feng & Xiaohua Liu

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  1. Yongyan Zhang
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  2. Jin Wu
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Correspondence to Xiaohua Liu.

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Supporting information The supporting information is available online at https://chem.scichina.com and https://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Zhang, Y., Wu, J., Ning, L. et al. Enantioselective synthesis of tetrasubstituted allenes via addition/arylation tandem reaction of 2-activated 1,3-enynes. Sci. China Chem. 66, 526–533 (2023). https://doi.org/10.1007/s11426-022-1443-5

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  • DOI: https://doi.org/10.1007/s11426-022-1443-5

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