Domino reactions of 5-deoxy-5-iodo- d- xylo- and - l-arabinofuranose derivatives with organometallic reagents. A way towards polyfunctionalized building-blocks

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.