| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1327650 | Journal of Organometallic Chemistry | 2006 | 13 Pages |
Novel type of Pd(II)-catalysed transformation of sugar-derived alkenitols furnishing 7-benzyloxy-2,5-dioxabicyclo[2.2.1]heptanes was discovered. The investigated bicyclisation displays an exceptional substrate selectivity towards xylo-configured unsaturated polyols. Moreover, a newly build stereogenic centre is formed in a diastereospecific cis-manner. The observed stereochemical preference was corroborated by modelling of pertinent transition states at the semiempirical level of theory (PM5). In addition, the single crystal X-ray analysis of an acylated analogue d-glycero-l-gulo-21 was done in order to establish the relative configuration of related bicyclic products.
Graphical abstractNew type of diastereoselective and substrate selective palladium(II)-catalysed bicyclisation of unsaturated polyols is described.Figure optionsDownload full-size imageDownload as PowerPoint slide
