Title of article
Novel bicyclisation of unsaturated polyols in PdCl2–CuCl2–AcOH catalytic system
Author/Authors
Matej Babjak، نويسنده , , L’ubo? Reme?، نويسنده , , Peter Szolcs?nyi، نويسنده , , Peter Z?lupsk?، نويسنده , , Du?an Miklo?، نويسنده , , Tibor Gracza، نويسنده ,
Issue Information
دوفصلنامه با شماره پیاپی سال 2006
Pages
13
From page
928
To page
940
Abstract
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.
Keywords
Palladium(II)-catalysis , Diastereoselectivity , substrate selectivity , Bicyclisation , Semiempirical calculations
Journal title
Journal of Organometallic Chemistry
Serial Year
2006
Journal title
Journal of Organometallic Chemistry
Record number
1379156
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