Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions.

In the presence of triethylsilyl trifluoromethanesulfonate and triethylamine, aliphatic nitriles undergo addition reactions with aldonitrones under non-basic, mild conditions, providing O-triethylsilyl ethers of β-N-hydroxyamino nitriles with high yield. The reaction appears to proceed through formation of an N-silyl ketene imine in situ followed by a Mannich-type reaction. [ABSTRACT FROM AUTHOR]