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.
Cyclopropanation of 5-Methylene Galactopyranosides by Dihalo-, Ethoxycarbonyl-, and Unsubstituted Carbenes
CHIACCHIO, MARIA ASSUNTA ROSSELLA;PISTARA', Venerando;RESCIFINA, Antonio;
2008-01-01
Abstract
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.File in questo prodotto:
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