Document Detail


Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor.
MedLine Citation:
PMID:  22543734     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer.
Authors:
Tyler A Davis; Michael W Danneman; Jeffrey N Johnston
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-04-30
Journal Detail:
Title:  Chemical communications (Cambridge, England)     Volume:  48     ISSN:  1364-548X     ISO Abbreviation:  Chem. Commun. (Camb.)     Publication Date:  2012 Jun 
Date Detail:
Created Date:  2012-05-11     Completed Date:  2012-08-27     Revised Date:  2014-08-17    
Medline Journal Info:
Nlm Unique ID:  9610838     Medline TA:  Chem Commun (Camb)     Country:  England    
Other Details:
Languages:  eng     Pagination:  5578-80     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alkanes / chemical synthesis,  chemistry*
Azo Compounds / chemical synthesis,  chemistry*
Catalysis
Glycine Plasma Membrane Transport Proteins / antagonists & inhibitors*
Humans
Nitro Compounds / chemical synthesis,  chemistry*
Protons
Stereoisomerism
Thiosemicarbazones / chemical synthesis,  chemistry*
Grant Support
ID/Acronym/Agency:
GM 084333/GM/NIGMS NIH HHS; R01 GM084333/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Alkanes; 0/Azo Compounds; 0/Glycine Plasma Membrane Transport Proteins; 0/Nitro Compounds; 0/Protons; 0/SLC6A9 protein, human; 0/Thiosemicarbazones; 0/azomethine
Comments/Corrections

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