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

Beilstein Journal of Organic Chemistry

Mike M. K. Boysen¹  Tobias Minuth¹ 

[1] Institute of Organic Chemistry, Gottfried-Wilhelm-Leibniz University of Hannover, Schneiderberg 1B, D-30167 Hannover, Germany;

关键词: asymmetric synthesis;    carbohydrates;    copper;    cyclopropanation;    ligand design;   

DOI  :  10.3762/bjoc.6.23

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown