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Synthesis of a new chiral cyclic aminal derived from rac-1,2-propanediamine
- 1.0384343 - FZÚ 2013 RIV GB eng J - Journal Article
Rivera, A. - Pacheco, D.J. - Ríos-Motta, J. - Fejfarová, Karla - Dušek, Michal
Synthesis of a new chiral cyclic aminal derived from rac-1,2-propanediamine.
Tetrahedron Letters. Roč. 53, č. 45 (2012), s. 6132-6135. ISSN 0040-4039. E-ISSN 1873-3581
Grant - others:AV ČR(CZ) AP0701
Program: Akademická prémie - Praemium Academiae
Institutional research plan: CEZ:AV0Z10100521
Keywords : aminal cage * axial chirality * imidazolidine-bridged bis(phenols) * Mannich condensation * 1,2-propanediamine
Subject RIV: BM - Solid Matter Physics ; Magnetism
Impact factor: 2.397, year: 2012
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.
Permanent Link: http://hdl.handle.net/11104/0214032
Number of the records: 1