Journal
TETRAHEDRON LETTERS
Volume 53, Issue 45, Pages 6132-6135Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.08.154
Keywords
Aminal cage; Axial chirality; Imidazolidine-bridged bis(phenols); Mannich condensation; 1,2-Propanediamine
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Funding
- Direccion de Investigaciones, Sede Bogota (DIB) de la Universidad Nacional de Colombia
- Fundacion para la Promocion de la Investigacion y la Tecnologia del Banco de la Republica
- Institute of Physics [AVOZ10100521]
- Academy of Sciences of the Czech Republic
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The cyclic aminal 4,9-dimethyl-1,3,6,8-tetraazatricyclo[4.4.1.1(3.8)]dodecane 4c was synthesized by the reaction of commercial rac-1,2-propanediamine with paraformaldehyde in an aqueous solution. H-1 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 2,2'-[(4-methylimidazolidine-1,3-diyl)dimethanediyl]bis(4-chlorophenol) 7 as a racemic mixture. The crystal structure of 7 was determined by single X-ray diffraction analysis. (C) 2012 Elsevier Ltd. All rights reserved.
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