Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions
Received: 09 April 2014
Accepted after revision: 07 May 2014
24 June 2014 (online)
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.
References and Notes
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