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Abstract

4-Hydroxyproline Containing Podands: New Chiral Catalysts of the Asymmetric Biginelli Reaction †

by
Yulia Titova
*,
Irina Ovchinnikova
,
Olga Fedorova
,
Gennady Rusinov
and
Valery Charushin
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 620990 Ekaterinburg, Russia
*
Author to whom correspondence should be addressed.
†
Presented at Symmetry 2017—The First International Conference on Symmetry, Barcelona, Spain, 16–18 October 2017.
Proceedings 2018, 2(1), 12; https://doi.org/10.3390/proceedings2010012
Published: 4 January 2018
(This article belongs to the Proceedings of The First International Conference on Symmetry)
Versions Notes
4-Aryl substituted dihydropyrimidines (DHPMs), the products of the multicomponent Biginelli reaction, are well known as cardiotropic, hypotensive, antitumor, anti-inflammatory, antifungal and antiviral agents. Considerable attention is paid to their asymmetric synthesis due to the fact that the pharmacological activity of enantiomers of chiral DHPMs can vary considerably.
Previously, we showed the prospects of using proline derivatives as chiral catalysts in the asymmetric Biginelli reaction [1,2].
Herein, we report the synthesis of new C2-symmetric chiral catalysts based on acyclic analogs of crown-ether (podands) and 4-hydroxyproline.
The combination of the S-shaped conformation of the polyester chain with the optically active centers of the proline fragment in C2-symmetric organocatalysts made it possible to obtain the product of the Biginelli reaction with 68–72% ee.

Acknowledgments

The work was financially supported by the Russian Science Foundation (project no. 15-13-00077 in the part of studying the asymmetric Biginelli reaction) and the Russian Foundation for Basic Research (project no. 16-29-10757-ofi_m in the part of synthesis of chiral catalysts).

References

  1. Fedorova, O.V.; Titova, Y.A.; Vigorov, A.Y.; Toporova, M.S.; Alisienok, O.A.; Murashkevich, A.N.; Krasnov, V.P.; Rusinov, G.L.; Charushin, V.N. Asymmetric Biginelli Reaction Catalyzed by Silicon, Titanium and Aluminum Oxides. Catal. Lett. 2016, 146, 493–498. [Google Scholar] [CrossRef]
  2. Titova, Y.; Fedorova, O.; Rusinov, G.; Vigorov, A.; Krasnov, V.; Murashkevich, A.; Charushin, V. Effect of nanosized TiO2–SiO2 covalently modified by chiral molecules on the asymmetric Biginelli reaction. Catal. Today 2015, 241, 270–274. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

Titova, Y.; Ovchinnikova, I.; Fedorova, O.; Rusinov, G.; Charushin, V. 4-Hydroxyproline Containing Podands: New Chiral Catalysts of the Asymmetric Biginelli Reaction. Proceedings 2018, 2, 12. https://doi.org/10.3390/proceedings2010012

AMA Style

Titova Y, Ovchinnikova I, Fedorova O, Rusinov G, Charushin V. 4-Hydroxyproline Containing Podands: New Chiral Catalysts of the Asymmetric Biginelli Reaction. Proceedings. 2018; 2(1):12. https://doi.org/10.3390/proceedings2010012

Chicago/Turabian Style

Titova, Yulia, Irina Ovchinnikova, Olga Fedorova, Gennady Rusinov, and Valery Charushin. 2018. "4-Hydroxyproline Containing Podands: New Chiral Catalysts of the Asymmetric Biginelli Reaction" Proceedings 2, no. 1: 12. https://doi.org/10.3390/proceedings2010012

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