Document Detail

Switching the Stereochemical Outcome of 6-endo-trig Cyclizations; Synthesis of 2,6-cis-6-Substituted-4-Oxo-Pipecolic Acids.
MedLine Citation:
PMID:  23126509     Owner:  NLM     Status:  Publisher    
A base mediated 6-endo-trig cyclization of readily accessible enone derived α-amino acids has been developed for the direct synthesis of novel 2,6-cis-6-substituted-4-oxo-L-pipecolic acids. A range of aliphatic and aryl side-chains were tolerated by this mild procedure to give the target compounds in good overall yields. Molecular modeling of the 6-endo-trig cyclization allowed some insight as to how these compounds were formed, with the enolate intermediate generated via an equilibrium process, followed by irreversible tautomerization/neutralization providing the driving force for product formation. Stereoselective reduction and deprotection of the resulting 2,6-cis-6-substituted-4-oxo-L-pipecolic acids to the corresponding 4-hydroxy-L-pipecolic acids was also performed.
Mark Daly; Alastair A Cant; Lindsay Sarah Fowler; Graham L Simpson; Hans Martin Senn; Andrew Sutherland
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-5
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:  2012-11-6     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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