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Mild Rhodium(III)‐Catalyzed Cyclization of Amides with α,β‐Unsaturated Aldehydes and Ketones to Azepinones: Application to the Synthesis of the Homoprotoberberine Framework
Author(s) -
Shi Zhuangzhi,
Grohmann Christoph,
Glorius Frank
Publication year - 2013
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.201301426
Subject(s) - annulation , chemistry , catalysis , rhodium , tandem , ring (chemistry) , intermolecular force , combinatorial chemistry , condensation , medicinal chemistry , organic chemistry , stereochemistry , molecule , materials science , physics , composite material , thermodynamics
Seven! The title reaction can be described as an intermolecular annulation involving tandem CH activation, cyclization to give the seven‐membered ring, and condensation steps. Biologically interesting azepinone derivatives can be prepared in this way. The synthetic potential of this method was demonstrated by the construction of the homoprotoberberine ring system.