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
Related Documents :
24630559 - Efficient synthesis of novel glutamate homologues and investigation of their affinity a...
19384269 - Syntheses, spectroscopic and afm characterization of some manganese porphyrins and thei...
24703219 - Development of new chiral ligand exchange capillary electrophoresis system with amino a...
18963729 - Synthesis and properties of a chelating resin containing triazolethiol groups.
18963089 - Selection of the counter-cation in the solvent extraction of anionic chelates: spectrop...
25117999 - Omega-3 supplementation during the first 5 years of life and later academic performance...
16701929 - The impact of uv-b and sulphur- or copper-containing solutions in acidic conditions on ...
23205249 - The effect of bacteria, enzymes and inulin on fermentation and aerobic stability of cor...
15202899 - Glucuronic acid derivatives as branching units for the synthesis of glycopeptide mimetics.
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:  -    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

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

Previous Document:  Bacterial and archaeal diversities in Yunnan and Tibetan hot springs, China.
Next Document:  Topical application of a film-forming emulgel dressing that controls the release of stratifin and ac...