A protecting-group-free two-step approach for the preparation of tetrahydroquinolines has been developed. The procedure involves a highly regio-and enantioselective intermolecular iridium-catalyzed allylic amination followed by one-pot hydroboration and intramolecular Suzuki-Miyaura cross-coupling. This method was applied in total syntheses of the alkaloids (+)-angustureine and (-)-cuspareine. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Satyanarayana Gedu

Department of Chemistry

D. Pflästerer

G. Helmchen

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IIT Hyderabad

European Journal of Organic Chemistry

Enantioselective syntheses of tetrahydroquinolines based on iridium-catalyzed allylic substitutions: Total syntheses of (+)-angustureine and (-)-cuspareine