Domino reactions of 5-deoxy-5-iodo-d-xylo- and -l-arabinofuranose derivatives with organometallic reagents. A way towards polyfunctionalized building-blocks |
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Authors: | Ariane Bercier Charles Portella |
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Institution: | Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims (I.C.M.R.), CNRS UMR 6229, U.F.R. Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France |
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Abstract: | Domino reactions involving metal-halogen exchange, furanose ring-opening and nucleophilic addition from 3-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-d-xylofuranose and the epimeric l-arabino derivative with various organometallic reagents are reported. In anhydrous conditions, with a large excess of organolithium or Grignard reagents, vicinal diols are obtained with good yields and a fair diastereoselectivity. Interestingly, with α-trimethylsilyl organolithium reagents, the fragmentation of the furanose ring to the substituted pent-4-enal is followed by a Peterson olefination giving dienic compounds in a four-step one-pot process. |
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Keywords: | Domino reactions d-xylofuranosides" target="_blank">d-xylofuranosides Metal-halogen exchange Organometallic reagents Peterson olefination |
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