Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral 1-halo-1-iodo alditols

C.C. Gonzalez, A.R. Kennedy, E.I. Leon, C. Riesco-Fagundo, E. Suarez

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Treatment of 1,2-fluorohydrins, 1,2-chlorohydrins, 1,2-bromohydrins, and 1,2-iodohydrins of the D-gluco, D-galacto, D-lacto, L-rhamno, D-allo, L-arabino, 3-deoxy-D-gluco, and 3,4-dideoxy-D-gluco families of carbohydrates with the (diacetoxyiodo)benzene/iodine system afforded 1-fluoro-1-iodo, 1-chloro-1-iodo, 1-bromo-1-iodo, and 1,1-diiodo alditols, respectively, in excellent yields. The reaction was achieved by radical fragmentation of the C1C2 bond, triggered by the initially formed anomeric alkoxy radical, and subsequent trapping of the C2-radical by iodine atoms. This methodology is compatible with the stability of the protective groups most frequently used in carbohydrate chemistry. The potential utility of these 1-halo-1-iodo alditols as chiral synthons was evaluated by their transformation into alk-1-enyl iodides and in the Takai E-olefination reaction.
Original languageEnglish
Pages (from-to)5800-5809
Number of pages9
JournalChemistry - A European Journal
Volume9
Issue number23
DOIs
Publication statusPublished - 5 Dec 2003

Keywords

  • halogen compounds
  • alditols
  • carbohydrates
  • iodine
  • radical reactions

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