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One out of Four: Kinetic Resolution of Stereoisomeric Mixtures of Secondary Alcohols with a Quaternary Carbon Atom in the β-Position by Cu-H-Catalyzed Enantioselective Silylation.

Zaneta PapadopuluNovid KazeroonianElisabeth IrranMartin Oestreich
Published in: ACS organic & inorganic Au (2021)
An enantio- and diastereoselective Cu-H-catalyzed silylation of acyclic secondary alcohols with a vicinal quaternary stereocenter is reported. The reaction kinetically selects one out of four stereoisomers, affording the fastest-reacting stereoisomer as the silyl ether in enantio- and diastereomerically enriched form. The obtained motif with a quaternary carbon atom in the β-position of the hydroxy group is otherwise not easy to access.
Keyphrases
  • room temperature
  • molecular dynamics
  • ionic liquid
  • electron transfer
  • aqueous solution
  • single molecule