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Palladium mediated cycloisomerization of sugar alkynols: synthesis of cyclic enol-ethers and spiroketals
Authors:CV Ramana  Rosy Mallik  Rajesh G Gonnade  Mukund K Gurjar
Institution:National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India
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.
Keywords:Palladium  Cycloisomerization  C-alkynylfuranose  Spiroketal  Enol-ether
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