Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones

作者：Yang Xintuo; Chen Pinhong; Liu Guosheng^*

来源：CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42(10): 3382-3389.

DOI：10.6023/cjoc202208021

• aza-Wacker
• palladium catalysis
• asymmetric aminopalladation
• chiral 1,3-oxazinan-2-ones
• chiral pyridinyloxazoline

A Pd-catalyzed asymmetric aza-Wacker-type reaction with N-Ts carbamate as the nucleophile has been developed, which employed a C-6 substituted pyridinyl-oxazoline as the chiral ligand and benzoquinone (BQ) as the oxidant. This reaction provides an efficient access to chiral 1,3-oxazinan-2-ones with good efficiency and excellent enantioselectivity. Mechanistic studies indicated that the reaction is initiated by an intramolecular asymmetric aminopalladation.

• 单位
  中国科学院研究生院