Organophotocatalysed synthesis of 2-piperidinones in one step via [1 + 2 + 3] strategy

Yi-Dan Du, Shan Wang, Hai-Wu Du, Xiao-Yong Chang, Xiao-Yi Chen, Yu-Long Li and Wei Shu ()
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Yi-Dan Du: Southern University of Science and Technology
Shan Wang: Southern University of Science and Technology
Hai-Wu Du: Southern University of Science and Technology
Xiao-Yong Chang: Southern University of Science and Technology
Xiao-Yi Chen: Southern University of Science and Technology
Yu-Long Li: Sichuan University of Science and Engineering
Wei Shu: Southern University of Science and Technology

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Six-membered N-containing heterocycles, such as 2-piperidinone derivatives, with diverse substitution patterns are widespread in natural products, drug molecules and serve as key precursors for piperidines. Thus, the development of stereoselective synthesis of multi-substituted 2-piperidinones are attractive. However, existing methods heavily rely on modification of pre-synthesized backbones which require tedious multi-step procedure and suffer from limited substitution patterns. Herein, an organophotocatalysed [1 + 2 + 3] strategy was developed to enable the one-step access to diverse substituted 2-piperidinones from easily available inorganic ammonium salts, alkenes, and unsaturated carbonyl compounds. This mild protocol exhibits exclusive chemoselectivity over two alkenes, tolerating both terminal and internal alkenes with a wide range of functional groups.

Date: 2023
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DOI: 10.1038/s41467-023-40197-x

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