Bis(oxazolines) based on glycopyranosides - Steric, configurational and conformational influences on stereoselectivity

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Minuth, Tobias; Boysen, Mike M. K.: Bis(oxazolines) based on glycopyranosides - Steric, configurational and conformational influences on stereoselectivity. In: Beilstein Journal of Organic Chemistry 6 (2010), 23. DOI: http://dx.doi.org/10.3762/bjoc.6.23

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Sum total of downloads: 55




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Abstract: 
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.
License of this version: CC BY 2.0
Document Type: article
Publishing status: publishedVersion
Issue Date: 2010
Appears in Collections:Naturwissenschaftliche Fakultät

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pos. country downloads
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1 image of flag of Germany Germany 49 89.09%
2 image of flag of Russian Federation Russian Federation 1 1.82%
3 image of flag of Netherlands Netherlands 1 1.82%
4 image of flag of Mongolia Mongolia 1 1.82%
5 image of flag of Georgia Georgia 1 1.82%
6 image of flag of China China 1 1.82%
7 image of flag of Switzerland Switzerland 1 1.82%

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