Efficient Synthesis of N-Alkylated 4-Pyridones by Copper-Catalyzed Intermolecular Asymmetric Propargylic Amination

Wen Shao; Ye Wang; Ze-Peng Yang; Xiao Zhang; Shu-Li You

doi:10.1002/asia.201800373

Efficient Synthesis of N-Alkylated 4-Pyridones by Copper-Catalyzed Intermolecular Asymmetric Propargylic Amination

Chem Asian J. 2018 May 4;13(9):1103-1107. doi: 10.1002/asia.201800373. Epub 2018 Apr 6.

Authors

Wen Shao¹, Ye Wang¹, Ze-Peng Yang¹, Xiao Zhang¹, Shu-Li You^{1

2}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
² Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China.

PMID: 29542867
DOI: 10.1002/asia.201800373

Abstract

Copper-catalyzed intermolecular asymmetric propargylic amination with 4-hydroxypyridines has been realized for the first time. In the presence of Cu complex derived from Pybox ligand, the N-propargylated 4-pyridones were obtained under mild reaction conditions with up to 99 % yield and 95 % ee. The Pybox ligand bearing a 4-F-phenyl substituent plays a key role for the high enantioselectivity. The products can be easily transformed to the core structure of quinolizidine alkaloids.

Keywords: 4-pyridone; amination; asymmetric catalysis; copper; propargylation.