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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F12%3A00377072" target="_blank" >RIV/68378271:_____/12:00377072 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.tetlet.2011.11.046" target="_blank" >http://dx.doi.org/10.1016/j.tetlet.2011.11.046</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tetlet.2011.11.046" target="_blank" >10.1016/j.tetlet.2011.11.046</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 speci?c 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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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 speci?c 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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

BM - Fyzika pevných látek a magnetismus

OECD FORD obor

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Projekt

—

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Tetrahedron Letters

ISSN

0040-4039

e-ISSN

—

Svazek periodika

53

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

4

Strana od-do

345-348

Kód UT WoS článku

000299582100021

EID výsledku v databázi Scopus

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