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Synthesis of a new chiral cyclic aminal derived from rac-1,2-propanediamine
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SYSNO ASEP 0384343 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis of a new chiral cyclic aminal derived from rac-1,2-propanediamine Author(s) Rivera, A. (CO)
Pacheco, D.J. (CO)
Ríos-Motta, J. (CO)
Fejfarová, Karla (FZU-D)
Dušek, Michal (FZU-D) RID, ORCID, SAISource Title Tetrahedron Letters. - : Elsevier - ISSN 0040-4039
Roč. 53, č. 45 (2012), s. 6132-6135Number of pages 4 s. Language eng - English Country GB - United Kingdom Keywords aminal cage ; axial chirality ; imidazolidine-bridged bis(phenols) ; Mannich condensation ; 1,2-propanediamine Subject RIV BM - Solid Matter Physics ; Magnetism CEZ AV0Z10100521 - FZU-D (2005-2011) UT WOS 000310760800037 DOI https://doi.org/10.1016/j.tetlet.2012.08.154 Annotation The cyclic aminal 4,9-dimethyl-1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane was synthesized by the reaction of rac-1,2-propanediamine with paraformaldehyde in an aqueous solution. 1H NMR analysis clearly revealed that the compound is chiral and racemic with an axis of chirality. To our knowledge, this is the first example of an azaadamantane derivative having axial chirality. This aminal was used in a Mannich type reaction with p-chlorophenol yielding 2,20-[(4-methylimidazolidine-1,3-diyl)dimethanediyl]bis(4-chlorophenol), which was determined by single X-ray diffraction analysis. Workplace Institute of Physics Contact Kristina Potocká, potocka@fzu.cz, Tel.: 220 318 579 Year of Publishing 2013
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