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Synthesis 1995; 1995(5): 566-570
DOI: 10.1055/s-1995-3953
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A Convenient Access to Chiral Monofunctionalized Bicyclic Guanidinium Receptor Groups

A. Metzger, W. Peschke, F. P. Schmidtchen*
  • *Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstraße 4, D-85747 Garching, Germany, Fax +49(89)32093345
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Publication Date:
31 December 2000 (online)

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An easy and high-yield route for the preparation of functional and chiral hexahydropyrimido[1,2-a]pyrimidines 3 is described. Starting from known methioninol and 2-methylmercaptotetrahydropyrimidine 5, the target compounds, which may be useful as building blocks in the synthesis of polymodular molecular hosts, were obtained in over 50% total yield. As an example the iodo compound 20 was converted into the homoarginine analog 22 in 70% yield.

molecular recognition - anion host - guanidine - amino acid - chiral pyrimido[1,2a]pyrimidine