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Nugent et al. protected these compounds with tert-butoxycarbonyl in a variant of the Henry reaction representing one of the first known chiral proton catalysis reactions discovered outside of proteins. They produce ketenes in the Wolff rearrangement, then react with those ketenes in the Staudinger cycloaddition. Both alkenes and tertiary alcohols yield a product that can rearrange to form them in the Schmidt reaction. Any reaction that uses them is denoted by the prefix "aza." Their namesake functional group is attacked by a cyanide ion in the Strecker synthesis of amino acids, and they are produced intramolecularly via the reduction of azides. Reacting carbonyl compounds with primary amines gives derivatives of these compounds known as Schiff bases. For 10 points, name these compounds characterized by the presence of a carbon-nitrogen double bond.
Nugent et al. protected these compounds with tert-butoxycarbonyl in a variant of the Henry reaction representing one of the first known chiral proton catalysis reactions discovered outside of proteins.
imines [accept Schiff bases until "Wolff" and grudgingly prompt afterwards]