Document Detail

Lewis Acid catalyzed dipolar cycloadditions of an activated imidate.
MedLine Citation:
PMID:  15549839     Owner:  NLM     Status:  PubMed-not-MEDLINE    
An evaluation of simple Lewis acids revealed that N-malonylimidates undergo catalyzed [3+2] cycloaddition reactions with aldehydes, imines, and activated olefins to form oxazolines, imidazolines, and pyrrolines, respectively. Reactions proceed optimally at ambient temperature with the addition of 5 mol % of MgCl(2) in CH(3)CN. Experiments aimed at elucidation of the reactive intermediate undergoing cycloaddition suggest that the Lewis acid promotes a 1,2-prototropic shift to give a metal-coordinated azomethine ylide, rather than ionization and proton transfer to give a nitrile ylide.
Roy K Bowman; Jeffrey S Johnson
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Nov 
Date Detail:
Created Date:  2004-11-19     Completed Date:  2005-01-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8537-40     Citation Subset:  -    
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
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