title: Carbohydrates as efficient catalysts for the hydration of α-amino nitriles.
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.
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: Sampada
authors.initials: S
authors.lastname: Chitale
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: Joshua S
authors.initials: JS
authors.lastname: Derasp
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: Bashir
authors.initials: B
authors.lastname: Hussain
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: Kashif
authors.initials: K
authors.lastname: Tanveer
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: André M
authors.initials: AM
authors.lastname: Beauchemin
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D009570:Nitriles / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D009570:Nitriles; D014867:Water