Document Detail


Direct enantioselective Brønsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and ketoacids.
MedLine Citation:
PMID:  20929214     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with γ- and δ-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).
Authors:
Chloe A Holloway; Michael E Muratore; R Lan Storer; Darren J Dixon
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Organic letters     Volume:  12     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-10-29     Completed Date:  2011-01-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4720-3     Citation Subset:  IM    
Affiliation:
School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
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MeSH Terms
Descriptor/Qualifier:
Acids / chemistry*
Acylation
Catalysis
Cyclization
Imines / chemistry*
Molecular Structure
Stereoisomerism
Tryptamines / chemistry*
Chemical
Reg. No./Substance:
0/Acids; 0/Imines; 0/Tryptamines

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


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