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

Autor: Du, Yi-Dan, Wang, Shan, Du, Hai-Wu, Chang, Xiao-Yong, Chen, Xiao-Yi, Li, Yu-Long, Shu, Wei
Předmět:
Zdroj: Nature Communications; 9/2/2023, Vol. 14 Issue 1, p1-9, 9p
Abstrakt: 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. The synthesis of 2-piperidinone derivatives remains challenging. Here, the authors develop an organophotocatalysed [1 + 2 + 3] strategy to enable the one-step access to diverse 2-piperidinones from ammonium salts, alkenes, and unsaturated carbonyl compounds. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index