Novel bicyclisation of unsaturated polyols in PdCl2-CuCl2-AcOH catalytic system |
| |
| Authors: | Matej Babjak Peter Szolcsányi Dušan Mikloš |
| |
| Institution: | a Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
b Department of Inorganic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic |
| |
| Abstract: | Novel type of Pd(II)-catalysed transformation of sugar-derived alkenitols furnishing 7-benzyloxy-2,5-dioxabicyclo2.2.1]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. |
| |
| Keywords: | Palladium(II)-catalysis Diastereoselectivity Substrate selectivity Bicyclisation Semiempirical calculations |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
