Next Article in Journal
Plumbagin, a Potent Naphthoquinone from Nepenthes Plants with Growth Inhibiting and Larvicidal Activities
Previous Article in Journal
Effect of Ceria Addition to Na2O-ZrO2 Catalytic Mixtures on Lignin Waste Ex-Situ Pyrolysis
Previous Article in Special Issue
Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis
Communication

Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction

Department of Biological Chemistry, Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Jordi Girona 18-26, E08034 Barcelona, Spain
Academic Editor: Rafael Chinchilla
Molecules 2021, 26(4), 826; https://doi.org/10.3390/molecules26040826
Received: 23 December 2020 / Revised: 1 February 2021 / Accepted: 3 February 2021 / Published: 5 February 2021
(This article belongs to the Special Issue Organocatalysis II: Bioinspired and Supramolecular Catalysts)
The binding and stabilizing effect of arginine residues in certain aldolases served as inspiring source for the development of a family of amino acylguanidine organocatalysts. Screening and optimization led to identify the threonine derivative as the most suitable catalyst for the asymmetric aldol addition of hydroxyacetone, affording the syn diastereomer in high ee. In contrast, the proline derivative yielded the anti diasteromer. MMFF models suggest the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates. View Full-Text
Keywords: guanidines; bioinspired catalysts; aldol reaction; hydroxyacetone; asymmetric catalysis; organocatalysis guanidines; bioinspired catalysts; aldol reaction; hydroxyacetone; asymmetric catalysis; organocatalysis
Show Figures

Graphical abstract

MDPI and ACS Style

Jimeno, C. Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction. Molecules 2021, 26, 826. https://doi.org/10.3390/molecules26040826

AMA Style

Jimeno C. Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction. Molecules. 2021; 26(4):826. https://doi.org/10.3390/molecules26040826

Chicago/Turabian Style

Jimeno, Ciril. 2021. "Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction" Molecules 26, no. 4: 826. https://doi.org/10.3390/molecules26040826

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop