Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity

In previous studies we found that the asymmetric induction of bis(oxazolines) based on D-glucosamine strongly depended on the steric demand of the 3-O-substituents. To further probe the impact of the 3-position of the pyranose scaffold, we prepared 3-epimerised and 3-defunctionalised versions of the...

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Autores principales: Minuth, Tobias, Boysen, Mike M K
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874406/
https://www.ncbi.nlm.nih.gov/pubmed/20502606
http://dx.doi.org/10.3762/bjoc.6.23
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author Minuth, Tobias
Boysen, Mike M K
author_facet Minuth, Tobias
Boysen, Mike M K
author_sort Minuth, Tobias
collection PubMed
description In previous studies we found that the asymmetric induction of bis(oxazolines) based on D-glucosamine strongly depended on the steric demand of the 3-O-substituents. To further probe the impact of the 3-position of the pyranose scaffold, we prepared 3-epimerised and 3-defunctionalised versions of these ligands as well as a 3-O-formyl derivative. Application of these new ligands in asymmetric cyclopropanation revealed strong steric and configurational effects of position 3 on asymmetric induction, further dramatic effects of the pyranose conformation were also observed.
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spelling pubmed-28744062010-05-25 Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity Minuth, Tobias Boysen, Mike M K Beilstein J Org Chem Full Research Paper In previous studies we found that the asymmetric induction of bis(oxazolines) based on D-glucosamine strongly depended on the steric demand of the 3-O-substituents. To further probe the impact of the 3-position of the pyranose scaffold, we prepared 3-epimerised and 3-defunctionalised versions of these ligands as well as a 3-O-formyl derivative. Application of these new ligands in asymmetric cyclopropanation revealed strong steric and configurational effects of position 3 on asymmetric induction, further dramatic effects of the pyranose conformation were also observed. Beilstein-Institut 2010-03-04 /pmc/articles/PMC2874406/ /pubmed/20502606 http://dx.doi.org/10.3762/bjoc.6.23 Text en Copyright © 2010, Minuth and Boysen https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Minuth, Tobias
Boysen, Mike M K
Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
title Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
title_full Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
title_fullStr Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
title_full_unstemmed Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
title_short Bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
title_sort bis(oxazolines) based on glycopyranosides – steric, configurational and conformational influences on stereoselectivity
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874406/
https://www.ncbi.nlm.nih.gov/pubmed/20502606
http://dx.doi.org/10.3762/bjoc.6.23
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