Document Detail


Access to alpha-substituted amino acid derivatives via 1,3-dipolar cycloaddition of alpha-amino ester derived nitrones.
MedLine Citation:
PMID:  20058891     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of alpha-ketoesters with N-benzylhydroxylamine. The cycloaddition reactions of these nitrones with different alkenes were investigated under thermal solvent-free conditions. Considering conversions, yields, and selectivities, alkyl vinyl ethers have proven to be valuable partners to achieve this transformation, which creates a tetrafunctionalized stereogenic quaternary center. From the adducts derived from vinyl ethers, a three-step access to highly functionalized alpha-substituted amino acid derivatives is described.
Authors:
Thanh Binh Nguyen; Alice Beauseigneur; Arnaud Martel; Robert Dhal; Mathieu Laurent; Gilles Dujardin
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Feb 
Date Detail:
Created Date:  2010-01-29     Completed Date:  2010-04-05     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  611-20     Citation Subset:  IM    
Affiliation:
UCO2M 6011 CNRS, Universite du Maine, 72085 Le Mans, France.
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MeSH Terms
Descriptor/Qualifier:
Alkenes / chemistry*
Amino Acids / chemical synthesis*,  chemistry
Cyclization
Esters
Magnetic Resonance Spectroscopy
Molecular Structure
Nitrogen Oxides / chemical synthesis*,  chemistry
Organic Chemistry Processes
Stereoisomerism
Structure-Activity Relationship
Vinyl Compounds / chemistry*
Chemical
Reg. No./Substance:
0/Alkenes; 0/Amino Acids; 0/Esters; 0/Nitrogen Oxides; 0/Vinyl Compounds; 0/nitrones; 109-93-3/vinyl ether

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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