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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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Article information


Submitted
15 Sep 2016
Accepted
14 Oct 2016
First published
14 Oct 2016

Chem. Commun., 2016,52, 13147-13150
Article type
Communication

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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