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Multicomponent Synthesis of Pyrroles from Cyclopropanes: A One‐Pot Palladium(0)‐Catalyzed Dehydrocarbonylation/Dehydration
Author(s) -
Humenny William J.,
Kyriacou Polydoros,
Sapeta Katarina,
Karadeolian Avedis,
Kerr Michael A.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201206177
Ring the changes : The cycloaddition of nitrones with 1‐carboallyloxy‐1‐carbomethoxycyclopropanes yields tetrahydro‐1,2‐oxazines, which in turn undergo a Tsuji dehydrocarbonylation to give dihydro‐1,2‐oxazines (see scheme; dba=dibenzylideneacetone). Addition of base to this reaction mixture results in clean conversion to pyrroles. The result is a flexible three‐component strategy for the synthesis of tetrasubstituted pyrroles.