Palladium mediated cycloisomerization of sugar alkynols: synthesis of cyclic enol-ethers and spiroketals |
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Authors: | CV Ramana Rosy Mallik Rajesh G Gonnade Mukund K Gurjar |
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Institution: | National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India |
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Abstract: | Functionalized bicyclic enol-ethers and spiroketals are prepared by Pd catalyzed cycloisomerization of 3-C-alkynylfuranosyl derivatives. Cycloisomerization of differently substituted alkyne derivatives revealed a preference for 6-endo-dig cyclization over 5-exo-dig if the substituent is not sufficiently electron withdrawing. The scope of these cycloisomerizations has been further extended by integrating with conjugate addition. |
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Keywords: | Palladium Cycloisomerization C-alkynylfuranose Spiroketal Enol-ether |
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