The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds

Org Biomol Chem. 2012 Jun 28;10(24):4692-5. doi: 10.1039/c2ob25595b. Epub 2012 May 17.

Abstract

A catalytic version of the Rabe electrophilic amination is presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement.