Alkylation of camphor and pinanone imines of 2-(aminomethyl)thiazole. Enantioselective synthesis of 2-(1-aminoalkyl)thiazoles

Article abstract of DOI:10.1055/s-1996-4259

A method is described for the enantioselective synthesis of 2-(1-aminoalkyl)thiazoles 6 via stereoselective alkylation of the carbanions of (+)-(R)-camphor and (-)-(1S, 2S, 5S)-2-hydroxypinan-3-one imines 2 and 3 derived from 2-(aminomethyl)thiazole (2-AMT, 1). Compounds 6 serve as α-amino aldehyde precursors via thiazolyl-to-formyl conversion.