Download PDF
Synlett 1990; 1990(9): 543-544
DOI: 10.1055/s-1990-21160
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of (R)-N-Tosylemeriamine via Chiral N-Tosylimidazolidin-2-ones

Giuliana Cardillo* , Mario Orena, Maurizio Penna, Sergio Sandri, Claudia Tomasini
  • *Centro per to Studi della Fisica delle Macromolecole, Dipartimento di Chimica "G. Ciamician", Università di Bologna, Via Selmi 2, I-40126 Bologna, Italy
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The total syntheses of 3,4-diaminobutanoic acid (1) and (R)-N-tosylemeriamine (2e; 4-trimethylammonio-3-tosylamino-butanoate) are described, starting from methyl 4-[(S)-(1-phenylethyl)amino]-2-butenoate (3) and tosyl isocyanate through an intramolecular Michael addition. The intermediate 5R and 5S 5-(methoxycarbonylmethyl)-3-[(S)-1-phenylethyl]-1-tosylimidazolidin-2-ones (4) and (5) are easily separated and their absolute configuration at C-5 is assigned by means of 1H NMR spectroscopy.