Login / Signup

Rigidified Bis(sulfonyl)ethylenes as Effective Michael Acceptors for Asymmetric Catalysis: Application to the Enantioselective Synthesis of Quaternary Hydantoins.

Leire VillaescusaIker HernándezLaura AzcuneAinhoa RudiJosé M MerceroAitor LandaMikel OiarbideClaudio Palomo
Published in: The Journal of organic chemistry (2023)
The catalytic, enantio- and diastereoselective addition of hydantoin surrogates II to "rigidified" vinylidene bis(sulfone) reagents is developed, thus overcoming the inability of commonly employed β-substituted vinylic sulfones to react. Adducts are transformed in enantioenriched 5,5-disubstituted hydantoins through hydrolysis and reductive desulfonylation processes providing new structures for eventual bioassays. Density functional theory studies that rationalize the observed reactivity and stereoselectivity trends are also provided.
Keyphrases
  • density functional theory
  • ionic liquid
  • molecular dynamics
  • molecular docking
  • high resolution
  • solar cells
  • case control
  • anaerobic digestion
  • solid state
  • visible light