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Search for "1,5-dicarbonyl" in Full Text gives 4 result(s) in Beilstein Journal of Organic Chemistry.

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

  • James Guevara-Pulido,
  • Fernando González-Pérez,
  • José M. Andrés and
  • Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

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  • low catalyst loadings and mild reaction conditions. This research focuses on the kinetic resolution of 1,5-dicarbonyl compounds using a retro-Michael reaction, co-catalyzed at room temperature with 20 mol % of the Jørgensen–Hayashi catalyst and PNBA. The study highlights the importance of conducting
  • the kinetic resolution at a concentration of approximately ten millimolar (mM) to prevent the Michael retro-Michael equilibrium from affecting the process. Keywords: 1,5-dicarbonyl; equilibrium; kinetic resolution; organocatalysis; retro-Michael; Introduction For many years, enantiomers have been
  • olefins with a wide range of nucleophiles, with many organocatalyzed asymmetric examples highlighted in the literature [23][24]. We have observed that the enantioenriched 1,5-dicarbonyl Michael adducts, synthesized via organocatalyzed reaction of cinnamaldehyde with benzyl phenyl ketone, undergo
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Published 03 Mar 2025

Addition of dithi(ol)anylium tetrafluoroborates to α,β-unsaturated ketones

  • Yu-Chieh Huang,
  • An Nguyen,
  • Simone Gräßle,
  • Sylvia Vanderheiden,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2018, 14, 515–522, doi:10.3762/bjoc.14.37

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  • building blocks. Herein we investigate the scope and limitations of dithi(ol)anyl TFBs for a fast generation of masked 1,5-dicarbonyl compounds similar to Michael additions using ketene dithioacetals without the use of stoichiometric amounts of metals or additional catalysts which have been proposed in
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Published 26 Feb 2018

Useful access to enantiomerically pure protected inositols from carbohydrates: the aldohexos-5-uloses route

  • Felicia D’Andrea,
  • Giorgio Catelani,
  • Lorenzo Guazzelli and
  • Venerando Pistarà

Beilstein J. Org. Chem. 2016, 12, 2343–2350, doi:10.3762/bjoc.12.227

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  • and 2.3 Hz) agree with four substituents in the equatorial position for the preferred conformer. A comparable example of intramolecular aldol condensation of a 1,5-dicarbonyl derivative has been reported by Tadano et al. [39]. Almost a sole aldol product was obtained in a good yield and was
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Published 08 Nov 2016

Conjugate addition–enantioselective protonation reactions

  • James P. Phelan and
  • Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

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  • (R2 = H, Ph 71.5:28.5 to 90.5:9.5 er). In 2010, the Kobayashi group reported the calcium-catalyzed Michael addition of dibenzylmalonate (86) to N-acryloyloxazolidinones 87 followed by enantioselective protonation of a chiral calcium enolate to access 1,5-dicarbonyl compounds 90 (Scheme 21) [44]. The
  • role of the phenol was not elucidated. 1,5-Dicarbonyl compounds 90 were accessed with excellent enantioselectivity for a variety of aliphatic α-substituents, and only when R was phenyl was there a significant loss of enantioselectivity (72% yield, 74:26 er). Organocatalysts Multiple groups have
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Published 15 Jun 2016
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