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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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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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creator	Álvarez-Dorta, Dimitri León, Elisa I Kennedy, Alan R Riesco-Fagundo, Concepción Suárez, Ernesto
description	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.
doi_str_mv	10.1002/anie.200803696
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source	Wiley-Blackwell Read & Publish Collection
subjects	1,2‐diketones Aldehydes - chemistry aldol reaction carbohydrates Carbohydrates - chemistry Cyclization Ketones - chemistry Molecular Structure Nucleosides - chemistry Photochemistry radicals Stereoisomerism
title	Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2-Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols
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