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New cyclic aminals derived from rac-trans-1,2-diaminocyclohexane: synthesis and crystal structure of racemic 1,8,10,12-tetraazatetracyclo[8.3.1.1..sup.8,12./sup.O.sup.2,7./sup.] pentadecane and a route to its enantiomerically pure (R,R) and (S,S) isomers
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SYSNO ASEP 0377072 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title New cyclic aminals derived from rac-trans-1,2-diaminocyclohexane: synthesis and crystal structure of racemic 1,8,10,12-tetraazatetracyclo[8.3.1.1.8,12O2,7] pentadecane and a route to its enantiomerically pure (R,R) and (S,S) isomers Author(s) Rivera, A. (CO)
Quiroga, D. (CO)
Jiménez-Cruz, L. (CO)
Fejfarová, Karla (FZU-D)
Dušek, Michal (FZU-D) RID, ORCID, SAISource Title Tetrahedron Letters. - : Elsevier - ISSN 0040-4039
Roč. 53, č. 3 (2012), s. 345-348Number of pages 4 s. Language eng - English Country GB - United Kingdom Keywords crystal structure ; X-ray diffraction ; Jana2006 ; chiral cyclic aminals Subject RIV BM - Solid Matter Physics ; Magnetism CEZ AV0Z10100521 - FZU-D (2005-2011) UT WOS 000299582100021 DOI 10.1016/j.tetlet.2011.11.046 Annotation New enantiomerically pure macrocyclic aminals (2R,7R)- and (2S,7S)-1,8,10,12-tetraazatetracyclo[8.3.1.1.8,12 O2,7] pentadecane were obtained by a three component reaction between their respective pure enantiomer of trans-1,2-diaminocyclohexane, ammonia, and formaldehyde. Additionally, the X-ray crystal structure of the racemic compound and the specific rotations of the racemic and optically pure compounds were determined. To further understand the synthetic utilities of both enantiomers, Mannich-type reactions with 1H-benzotriazole were performed, affording (3aR,7aR)- and (3aS,7aS)-1,1! 0 -{[2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}bis-1H-benzotriazole and allowing for new possibilities related to the preparation of chiral ligands for asymmetric catalysis. Workplace Institute of Physics Contact Kristina Potocká, potocka@fzu.cz, Tel.: 220 318 579 Year of Publishing 2013
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