Document Detail


Synthesis of Enantioenriched Aza-Proline Derivatives Through Gold(I)-Catalyzed Cyclization of Chiral alpha-Hydrazino Esters.
MedLine Citation:
PMID:  23167735     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A selective gold(I)-catalyzed synthesis of chiral aza-proline derivatives has been developed by ring closure of enantioenriched alpha-hydrazino esters bearing an alkyne group. These are easily prepared through a synthetic strategy involving two key steps: organocatalyzed electrophilic amination of pent-4-ynal with dialkyl azodicarboxylate promoted by L-Proline and functionalization of the triple bond by Sonogashira cross-coupling. This strategy allowed the preparation of a range of enantioenriched alpha-hydrazino esters which underwent ring closure by using Ph3PAuCl/AgBF4 as a catalytic system. Under these conditions, 5-exo-dig cyclization was favored over 6-endo-dig and aza-proline derivatives were obtained in good yields without epimerization at the stereogenic center. Influence of the catalytic system, hydrazine protecting group and alkyne substitution on the cyclization step has also been investigated.
Authors:
Sébastien Bouvet; Xavier Moreau; Vincent Coeffard; Christine Greck
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-20
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-21     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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