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Bromoallenes as Synthetic Equivalents of Allyl Dications: Synthesis of Medium‐Sized Nitrogen Heterocycles through the Cyclization of Bromoallenes in the Presence of a Palladium( 0 ) Catalyst and an Alcohol
Author(s) -
Ohno Hiroaki,
Hamaguchi Hisao,
Ohata Miyo,
Tanaka Tetsuaki
Publication year - 2003
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.200250589
Subject(s) - chemistry , allene , palladium , moiety , catalysis , nucleophile , dication , allyl alcohol , alcohol , intramolecular force , stereoselectivity , medicinal chemistry , nitrogen atom , stereochemistry , organic chemistry , molecule , ring (chemistry)
A highly regio‐ and stereoselective synthesis of medium‐sized nitrogen heterocycles has been developed (see scheme), based on the discovery that bromoallenes can act as an allyl dication equivalent in the presence of a palladium( 0 ) catalyst and an alcohol. The intramolecular nucleophilic attack takes place exclusively at the central carbon atom of the allene moiety.