Carbohydrates as efficient catalysts for the hydration of α-amino nitrilesElectronic supplementary information (ESI) available: Selected optimization data, complete experimental procedures, characterization data, and NMR spectra. See DOI: 10.1039/c6cc07530d

• Main Authors: Chitale, Sampada, Derasp, Joshua S, Hussain, Bashir, Tanveer, Kashif, Beauchemin, André M
• Format: Article
• Language: English
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c6cc07530d

Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable. A general procedure for the alkaline hydration of α-amino nitriles has been developed using formaldehyde as catalyst.