The Development of a Catalytic Synthesis of Münchnones: A Simple Four-Component

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Mesoionic 1,3-oxazolium-5-oxides (e.g., Munchnones, 1), and their -amide substituted ketene tautomer (1'), are an important family of substrates for the synthesis of biologically relevant molecules. Munchnones are versatile 1,3-dipolar addition substrates and have proven key in the construction of a range of natural products and pharmacologically relevant heterocycles, including pyrroles,1,2a,b imidazoles,2c,d pyrrolines,2e and indole derivatives.2f Alternatively, the less stable ketene 1' can serve as a precursor to -amino acid and peptide derivatives, via reaction with alcohols or N-terminated peptides,3a and their cycloaddition with imines provides access to peptide-based -lactams.

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Author(s): 
Rajiv Dhawan, Rania D. Dghaym, Bruce A. Arndtsen
Journal: 
Journal of The Amirican Chemical Society, January 18, 2003
Copyright: 
Copyright © American Chemical Society