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Issue 89, 2016
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Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

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Abstract

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.

Graphical abstract: Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

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Publication details

The article was received on 15 Sep 2016, accepted on 14 Oct 2016 and first published on 14 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07530D
Citation: Chem. Commun., 2016,52, 13147-13150
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    Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

    S. Chitale, J. S. Derasp, B. Hussain, K. Tanveer and A. M. Beauchemin, Chem. Commun., 2016, 52, 13147
    DOI: 10.1039/C6CC07530D

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