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Asymmetric Construction of α-Substituted β-Hydroxy Lactones via Ni Catalyzed Decarboxylative Addition Reaction.

Lingchen HeEbrahim-Alkhalil M A AhmedHongxin LiuXingen HuHong-Ping XiaoJuan LiJun Jiang
Published in: The Journal of organic chemistry (2021)
We described a Ni-bidentate oxazoline catalyzed highly enantio- and diastereoselective decarboxylative aldol reaction of 2-oxotetrahydrofuran-3-carboxylic acid/2-oxochromane-3-carboxylic acid derivatives with different kinds of carbonyls. Under optimal reaction conditions, α-substituted β-hydroxy butyrolactones and dihydrocoumarins with an all-carbon quaternary stereocenter have been generated with high levels of functional-group compatibility. Furthermore, proficient transformations of products were also described, in which an aliphatic tertiary alcohol and a multi-substituted 1,4-diol were smoothly constructed through hydrogenation and ring-opening reaction, respectively.
Keyphrases
  • molecular docking
  • room temperature
  • electron transfer
  • visible light
  • transition metal