Synthesis of Bifunctional Amine-Squaramide Organocatalysts Derived from 3-((Dimethylamino)methylene)camphor

Uroš Grošelj; Luka Ciber; Helena Brodnik; Franc Požgan; Jurij Svete; Bogdan Štefane

doi:10.17344/acsi.2024.8757

Authors

Uroš Grošelj University of Ljubljana, Faculty of Chemistry and Chemical Technology Večna pot 113 P. O. Box 537 1001 Ljubljana Slovenia http://orcid.org/0000-0002-5186-9879
Luka Ciber Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia https://orcid.org/0000-0002-6631-1974
Helena Brodnik Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia https://orcid.org/0000-0002-0099-2236
Franc Požgan Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia https://orcid.org/0000-0001-6040-294X
Jurij Svete Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia https://orcid.org/0000-0003-3339-3595
Bogdan Štefane Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia https://orcid.org/0000-0002-8709-9853

DOI:

https://doi.org/10.17344/acsi.2024.8757

Abstract

Four bifunctional, noncovalent amine-squaramide organocatalysts were prepared from camphor in five steps. The stereochemistry of the prepared catalysts was thoroughly analyzed using various spectroscopic techniques. Their organocatalytic activity was investigated in the Michael addition of acetylacetone to trans-β-nitrostyrene. The addition product was formed in complete conversion and with an enantioselectivity of up to 77% ee. In the reactions catalyzed by the 2-exo-3-endo catalysts, the major (S)-enantiomer was formed, whereas in the presence of 2-endo-3-endo catalysts, the (R)-enantiomer was formed as the major product.

Author Biography

Uroš Grošelj, University of Ljubljana, Faculty of Chemistry and Chemical Technology Večna pot 113 P. O. Box 537 1001 Ljubljana Slovenia

Chair of Organic chemistry

Synthesis of Bifunctional Amine-Squaramide Organocatalysts Derived from 3-((Dimethylamino)methylene)camphor

Authors

DOI:

Abstract

Author Biography

Uroš Grošelj, University of Ljubljana, Faculty of Chemistry and Chemical Technology Večna pot 113 P. O. Box 537 1001 Ljubljana Slovenia

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