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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

BM - Solid-state physics and magnetism

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2012

Confidentiality

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

Name of the periodical

Tetrahedron Letters

ISSN

0040-4039

e-ISSN

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Volume of the periodical

53

Issue of the periodical within the volume

3

Country of publishing house

GB - UNITED KINGDOM

Number of pages

4

Pages from-to

345-348

UT code for WoS article

000299582100021

EID of the result in the Scopus database

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