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Synthesis 1996; 1996(5): 641-646
DOI: 10.1055/s-1996-4259
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Alkylation of Camphor and Pinanone Imines of 2-(Aminomethyl)thiazole. Enantioselective Synthesis of 2-(1-Aminoalkyl)thiazoles

Alessandro Dondoni1 , Francisco L. Merchan, Pedro Merino, Isabel Rojo, Tomas Tejero2
  • 1Laboratorio di Chimica Organica, Dipartimento di Chimica, Università di Ferrara, Via L. Borsari, 46, I-44100 Ferrara, Italy, Fax +39(532)240709
  • 2Departamento de Quimica Organica, ICMA, Universidad de Zaragoza, CSIC, Zaragoza, Spain
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Publication Date:
31 December 2000 (online)

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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.

2-aminomethylthiazole - α-aminocarbanions - α-amino-2-alkylthiazoles - asymmetric alkylation