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. © 2012 The Royal Society of Chemistry.
The Rabe amination after a century: Direct addition of N-heterocycles to carbonyl compounds / SCARPINO SCHIETROMA, DANIELE MARIA; Mattia R., Monaco; Valerio, Bucalossi; P. E., Walter; Gentili, Patrizia; Bella, Marco. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 10:24(2012), pp. 4692-4695. [10.1039/c2ob25595b]
The Rabe amination after a century: Direct addition of N-heterocycles to carbonyl compounds
SCARPINO SCHIETROMA, DANIELE MARIA;GENTILI, Patrizia;BELLA, Marco
2012
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. © 2012 The Royal Society of Chemistry.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
