Synthesis of (R)-N-Tosylemeriamine via ChiralN-Tosylimidazolidin-2-ones
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (09) , 543-544
- https://doi.org/10.1055/s-1990-21160
Abstract
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.Keywords
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