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

Giuliana Cardillo; Mario Orena; Maurizio Penna; Sergio Sandri; Claudia Tomasini

doi:10.1055/s-1990-21160

Synlett 1990; 1990(9): 543-544
DOI: 10.1055/s-1990-21160

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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

Abstract

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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.

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