Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols

D. Alvarez-Dorta, E.I. Leon, A.R. Kennedy, C. Riesco-Fagundo, E. Suarez

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Opened and closed: Visible-light photostimulation of 2,3-diuloses I triggers an unprecedented sequential rearrangement: A Norrish type II photoelimination to give an isolable acyclic photoenol intermediate II is followed by an intramolecular enolexo aldolization. The contraction of the pyranose ring in this process leads to a new type of cyclopentitol derivative III. R=acyl, alkyl, silyl group.
Original languageEnglish
Pages (from-to)8917-8919
Number of pages2
JournalAgewandte Chemie-International Edition
Volume47
Issue number46
DOIs
Publication statusPublished - 2008

Keywords

  • 1
  • 2-diketones
  • aldol reaction
  • carbohydrates
  • photochemistry
  • radicals

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