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

14 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.
LanguageEnglish
Pages8917-8919
Number of pages2
JournalAgewandte Chemie-International Edition
Volume47
Issue number46
DOIs
Publication statusPublished - 2008

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Cyclization
Carbohydrates
Derivatives
Light
3-hydroxybutanal

Keywords

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

Cite this

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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.",
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Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols. / Alvarez-Dorta, D.; Leon, E.I.; Kennedy, A.R.; Riesco-Fagundo, C.; Suarez, E.

In: Agewandte Chemie-International Edition, Vol. 47, No. 46, 2008, p. 8917-8919.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols

AU - Alvarez-Dorta, D.

AU - Leon, E.I.

AU - Kennedy, A.R.

AU - Riesco-Fagundo, C.

AU - Suarez, E.

PY - 2008

Y1 - 2008

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KW - 1

KW - 2-diketones

KW - aldol reaction

KW - carbohydrates

KW - photochemistry

KW - radicals

UR - http://dx.doi.org/10.1002/anie.200803696

U2 - 10.1002/anie.200803696

DO - 10.1002/anie.200803696

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EP - 8919

JO - Angewandte Chemie International Edition

T2 - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

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