Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2-Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols

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...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-01, Vol.47 (46), p.8917-8919
Main Authors: Álvarez-Dorta, Dimitri, León, Elisa I, Kennedy, Alan R, Riesco-Fagundo, Concepción, Suárez, Ernesto
Format: Article
Language:English
Subjects:
1,2‐diketones
Aldehydes - chemistry
aldol reaction
carbohydrates
Carbohydrates - chemistry
Cyclization
Ketones - chemistry
Molecular Structure
Nucleosides - chemistry
Photochemistry
radicals
Stereoisomerism
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803696