One-Pot Synthesis of Isoquinolinium Salts by Rhodium-Catalyzed CH Bond Activation: Application to the Total Synthesis of Oxychelerythrine

It's worth its salt: The title reaction leads to the synthesis of highly substituted isoquinolinium salts (see scheme; Cp*=Me5C5). The reaction proceeds through a CH activation and a subsequent annulation in the presence of a rhodium catalyst. The reaction mechanism is discussed as well as its...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-01, Vol.51 (1), p.197-200
Hauptverfasser:	Jayakumar, Jayachandran, Parthasarathy, Kanniyappan, Cheng, Chien-Hong
Format:	Artikel
Sprache:	eng
Schlagworte:	alkynes Alkynes - chemistry Amines - chemistry annulation Benzaldehydes - chemistry Benzophenanthridines - chemical synthesis Benzophenanthridines - chemistry Carbon - chemistry Catalysis Cyclization CH activation heterocycles Hydrogen - chemistry Isoquinolines - chemical synthesis Isoquinolines - chemistry rhodium Rhodium - chemistry Salts - chemistry
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Beschreibung
Zusammenfassung:	It's worth its salt: The title reaction leads to the synthesis of highly substituted isoquinolinium salts (see scheme; Cp*=Me5C5). The reaction proceeds through a CH activation and a subsequent annulation in the presence of a rhodium catalyst. The reaction mechanism is discussed as well as its application to the synthesis of the natural product oxychelerythrine.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201105755