Document Detail


Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern.
MedLine Citation:
PMID:  15575756     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH(4))(2)CO(3)-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.
Authors:
Tahar Ayad; Vanessa Faugeroux; Yves Génisson; Chantal André; Michel Baltas; Liliane Gorrichon
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Dec 
Date Detail:
Created Date:  2004-12-03     Completed Date:  2005-02-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8775-9     Citation Subset:  IM    
Affiliation:
Laboratoire Synthèse et Physicochimie des Molécules d'Intéret Biologique, UMR 5068 CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 04, France.
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MeSH Terms
Descriptor/Qualifier:
Cyclization
Epoxy Compounds / chemical synthesis,  chemistry
Hexanols / chemical synthesis*
Hydrolysis
Molecular Conformation
Stereoisomerism
Chemical
Reg. No./Substance:
0/4-aminohex-5-ene-1,2,3-triol; 0/Epoxy Compounds; 0/Hexanols

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