Enone-alkyne reductive coupling: a versatile entry to substituted pyrroles |
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Authors: | Thompson Benjamin B Montgomery John |
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Institution: | Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA. |
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Abstract: | The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dicarbonyl intermediate are avoided. Classes of pyrroles that are accessible by this approach include 2,3-, 2,4-, 1,2,3-, 1,2,4-, 2,3,5-, and 1,2,3,5-substituted monocyclic pyrroles as well as a number of fused-ring polycyclic derivatives. |
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