Enantio- and Diastereoselective NHC/Ni-Catalyzed Reductive Coupling of Alkenes with Carbonyls: Synthesis of Optically Active Indanols

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Abstract
We report a highly enantio- and diastereoselective reductive coupling of unactivated alkenes with aldehydes catalyzed by an N-heterocyclic carbene (NHC)/nickel complex, which provides efficient access to optically active indanol derivatives. Under mild conditions, a broad range of substrates bearing diverse functional groups─including electron-donating, electron-withdrawing, and heteroaromatic substituents─underwent smooth coupling to afford the corresponding products with excellent stereocontrol (all >99:1 dr, up to 97% ee). The method was also successfully extended to ketone substrates, delivering chiral tertiary alcohol derivatives with good enantioselectivity, further demonstrating its synthetic versatility. The use of a bulky chiral NHC ligand proved to be essential for achieving high stereoselectivity in the nickel-catalyzed process.
Funding Information
  • Science and Technology Commission of Shanghai Municipality (25ZR1402566)
  • National Natural Science Foundation of China (22325110)
  • National Natural Science Foundation of China (22501291)
  • Chinese Academy of Sciences (XDA0540000)
  • Chinese Academy of Sciences (XDB0610000)

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