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

0377072 - FZÚ 2013 RIV GB eng J - Článek v odborném periodiku
Rivera, A. - Quiroga, D. - Jiménez-Cruz, L. - Fejfarová, Karla - Dušek, Michal
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.^8,12O^2,7] pentadecane and a route to its enantiomerically pure (R,R) and (S,S) isomers.
Tetrahedron Letters. Roč. 53, č. 3 (2012), s. 345-348. ISSN 0040-4039. E-ISSN 1873-3581
Grant ostatní: AV ČR(CZ) AP0701
Program: Akademická prémie - Praemium Academiae
Výzkumný záměr: CEZ:AV0Z10100521
Klíčová slova: crystal structure * X-ray diffraction * Jana2006 * chiral cyclic aminals
Kód oboru RIV: BM - Fyzika pevných látek a magnetismus
Impakt faktor: 2.397, rok: 2012

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.
Trvalý link: http://hdl.handle.net/11104/0209326