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1.
  • Cele, Zamani E. D., et al. (author)
  • Catalytic asymmetric carbon-carbon bond forming reactions catalyzed by tetrahydroisoquinoline (TIQ) N,N '-dioxide ligands
  • 2013
  • In: Tetrahedron. - : Elsevier BV. - 0957-4166 .- 1362-511X. ; 24:4, s. 191-195
  • Journal article (peer-reviewed)abstract
    • The use of TIQ-N,N'-dioxide ligands in asymmetric C-C bond forming reactions is described. In the Michael addition of cyclohexane-1,3-dione and malonates to beta,gamma-unsaturated alpha-ketoesters, excellent yields (up to 93%) and moderate to good enantioselectivities (70-89% ee) were obtained. The catalytic hetero-ene reaction of 2-methoxypropene with phenylglyoxal gave the ene product in excellent yield (95%) with moderate enantioselectivity (77% ee). The catalyst system performed well at temperatures ranging from 0 to 30 degrees C and relatively low catalyst loading (0.2-5 mol %) with dichloromethane being the preferred solvent for all reactions.
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2.
  • Chakka, Sai Kumar, et al. (author)
  • Asymmetric conjugate addition of thioglycolate to a range of chalcones using tetrahydroisoquinoline (TIQ) N,N '-dioxide ligands
  • 2012
  • In: Tetrahedron. - : Elsevier BV. - 0957-4166 .- 1362-511X. ; 23:8, s. 616-622
  • Journal article (peer-reviewed)abstract
    • A series of novel TIQ based N,N'-oxide ligands were synthesised and screened for their catalytic activity in the enantioselective conjugate addition of thioglycolate to chalcones. Bulky groups on the side chain of the TIQ backbone provided the highest enantioselectivity of up to 88% with 10 mol % catalyst loading. It was also observed that these reactions proceeded optimally in the presence of dichloromethane as a solvent. Screening of various metals emphasized La(OTf)(3) as the ideal pre-catalyst for this particular reaction.
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