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Diastereo- and Enantioselective Construction of Spirocycles by Nickel-Catalyzed Cascade Borrowing Hydrogen Cyclization.

Zhengtian DingYiming WangWenfeng LiuYate ChenWangqing Kong
Published in: Journal of the American Chemical Society (2020)
Spirocycles play an important role in drug discovery and development owing to their inherent three-dimensionality and structural novelty. Despite the recent significant progress, the straightforward catalytic asymmetric assembly of spirocyclic scaffolds with multiple stereocenters from readily available starting materials remains a formidable challenge. Herein, we develop an unprecedented nickel-catalyzed one-pot synthesis of enantioenriched spiroindanones from easily available 1,6-enynes and o-formylarylboronic acids. The reaction proceeds smoothly under redox-neutral conditions, without the need for an additional hydrogen donor, and features a broad substrate scope and excellent regio-, enantio-, and diastereoselectivity.
Keyphrases
  • drug discovery
  • room temperature
  • reduced graphene oxide
  • oxide nanoparticles
  • carbon nanotubes
  • metal organic framework
  • visible light
  • electron transfer
  • gold nanoparticles
  • ionic liquid
  • structural basis
  • solid state