biostudies-literatureUnknown6Minuth TIn 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 journal of organic chemistry23https://www.ebi.ac.uk/biostudies/studies/S-EPMC2874406biostudies-literatureBis(oxazolines) based on glycopyranosides - steric, configurational and conformational influences on stereoselectivity.PMC2874406Boysen MMMinuth TfalseBis(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 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.2010-01-01T00:00:00Z2010 Mar2021-02-25T08:37:43Z2019-03-27T00:30:57ZS-EPMC28744062050260610.3762/bjoc.6.23