1,3-Dipolar Cycloaddition of D-Xylose Derived Nitrone with Methyl Acrylate and its Utilization in Synthesis of Chiral Polyhydroxylated Pyrrolidinones and Pyrrolidines

Podolan, Gabriel, Fišera, Ľubor and Prónayová, Naďa 1,3-Dipolar Cycloaddition of D-Xylose Derived Nitrone with Methyl Acrylate and its Utilization in Synthesis of Chiral Polyhydroxylated Pyrrolidinones and Pyrrolidines Acta Chimica Slovaca, Vol.1, No. 1, 2008, -

Document type: Článok z časopisu / Journal Article
Collection: Acta Chimica Slovaca  
 
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Author(s) Podolan, Gabriel
Fišera, Ľubor
Prónayová, Naďa
Title 1,3-Dipolar Cycloaddition of D-Xylose Derived Nitrone with Methyl Acrylate and its Utilization in Synthesis of Chiral Polyhydroxylated Pyrrolidinones and Pyrrolidines
Journal name Acta Chimica Slovaca
Publication date 2008
Year available 2008
Volume number 1
Issue number 1
ISBN 978-80-227-2957-4
Place of publication Bratislava
Publisher Slovak Technical University
Collection year 2008
Language english
Subject 250000 Chemical Sciences
250300 Organic Chemistry
250400 Analytical Chemistry
Abstract/Summary The cycloaddition of the chiral nitrone IV derived from D-xylose with methyl acrylate proceeded with very good diastereoselectivity for the anti-trans isoxazolidine Va. Its subsequent transformations to novel chiral polyhydroxylated pyrrolidinones and pyrrolidines are described. The results show that the method has potential use in the preparation of pyrrolidinones and pyrrolidines containing carbohydrate residues.
Keyword(s) chiral nitrones
pyrrolidines
cycloadditions
 
 
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