Novel bicyclisation of unsaturated polyols in PdCl2-CuCl2-AcOH catalytic system
Novel bicyclisation of unsaturated polyols in PdCl2-CuCl2-AcOH catalytic system
复制标题
DOI：
10.1016/j.jorganchem.2005.10.036
复制
发表时间：
2006-02-15
影响因子：
2.3
通讯作者：
Gracza, T
中科院分区：
文献类型：
--
作者：
Babjak, M;Remen, L;Gracza, T
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. (c) 2005 Elsevier B.V. All rights reserved.
