Cyclopropanation reactions of 6-deoxyhex-5-enopyranosides by methylene-zinc-iodide complex, dichlorocarbene, and rhodium ethoxycarbonyl complex addition afford optimum yields of the corresponding spirocyclopropanes. Surprisingly, a stereospecific spirocyclopropane derivative with the two halogens on the upper face of the 4-hydroxy substituent is obtained. To get more insight on the dichlorocarbene cyclopropanation process a computational study, based on DFT quantomechanic calculation was conducted.
|Titolo:||Cyclopropanation of 5-Methylene Galactopyranosides by Dihalo-, Ethoxycarbonyl-, and Unsubstituted Carbenes|
|Data di pubblicazione:||2008|
|Appare nelle tipologie:||1.1 Articolo in rivista|