Synthesis of a new chiral cyclic aminal derived from rac-1,2-propanediamine

0384343 - FZÚ 2013 RIV GB eng J - Článek v odborném periodiku
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 ostatní: AV ČR(CZ) AP0701
Program: Akademická prémie - Praemium Academiae
Výzkumný záměr: CEZ:AV0Z10100521
Klíčová slova: aminal cage * axial chirality * imidazolidine-bridged bis(phenols) * Mannich condensation * 1,2-propanediamine
Kód oboru RIV: BM - Fyzika pevných látek a magnetismus
Impakt faktor: 2.397, rok: 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.
Trvalý link: http://hdl.handle.net/11104/0214032