Non-biaryl atropisomers derived from carbohydrates. Part 3: Rotational isomerism of sterically hindered heteroaryl imidazolidine-2-ones and 2-thiones
Non-biaryl atropisomers derived from carbohydrates. Part 3: Rotational isomerism of sterically hindered heteroaryl imidazolidine-2-ones and 2-thiones
The present work describes in detail the preparation and structural characterization of a series of heteroaryls in which an o,o?-disubstituted phenyl ring is connected through a single C–N bond to a heterocyclic fragment of a chiral imidazolidine-2-one or 2-thione. As a consequence of hindered rotation, some of these substances exist as stable rotamers at room temperature and can easily be separated and characterized. Molecular mechanic calculations have also been carried out to evaluate the barriers to rotation.
atropisomerism, carbohydrates, imidazolidines, molecular mechanics, rotational isomers, derivatives, transformation, stereocontrol, isocyanates, reagents, barriers, behavior, amides, bond
7931-7944
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Silvero, Guadalupe
8e6975cc-88ec-4809-8040-bc84413d57d6
15 August 2005
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Silvero, Guadalupe
8e6975cc-88ec-4809-8040-bc84413d57d6
Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, Hursthouse, Michael B., Jiménez, José L., Light, Mark E., Palacios, Juan C. and Silvero, Guadalupe
(2005)
Non-biaryl atropisomers derived from carbohydrates. Part 3: Rotational isomerism of sterically hindered heteroaryl imidazolidine-2-ones and 2-thiones.
Tetrahedron, 61 (33), .
(doi:10.1016/j.tet.2005.06.017).
Abstract
The present work describes in detail the preparation and structural characterization of a series of heteroaryls in which an o,o?-disubstituted phenyl ring is connected through a single C–N bond to a heterocyclic fragment of a chiral imidazolidine-2-one or 2-thione. As a consequence of hindered rotation, some of these substances exist as stable rotamers at room temperature and can easily be separated and characterized. Molecular mechanic calculations have also been carried out to evaluate the barriers to rotation.
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Published date: 15 August 2005
Keywords:
atropisomerism, carbohydrates, imidazolidines, molecular mechanics, rotational isomers, derivatives, transformation, stereocontrol, isocyanates, reagents, barriers, behavior, amides, bond
Identifiers
Local EPrints ID: 20707
URI: http://eprints.soton.ac.uk/id/eprint/20707
ISSN: 0040-4020
PURE UUID: 3aef2c25-123b-4141-ae14-06adb656a614
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Date deposited: 28 Feb 2006
Last modified: 16 Mar 2024 03:04
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Contributors
Author:
Martín Ávalos
Author:
Reyes Babiano
Author:
Pedro Cintas
Author:
José L. Jiménez
Author:
Juan C. Palacios
Author:
Guadalupe Silvero
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