Synfacts 2007(5): 0509-0509  
DOI: 10.1055/s-2007-968461
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereochemical Outcome of a Palladium-Catalyzed Annulation

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
A. Rudolph, N. Rackelmann, M. Lautens*
University of Toronto, Canada
Further Information

Publication History

Publication Date:
24 April 2007 (online)


Extending their previous methodology (J. Am. Chem. Soc. 2005, 127, 13148-13149), the authors report the Pd-catalyzed intramolecular annulation of secondary alkyl iodides to give fused bicylic and tricyclic products. Given the paucity of work on the stereochemical outcome of reactions involving oxidative addition from a Pd(II) to a Pd(IV) intermediate, mechanistic studies were undertaken. Using chiral substrates, annulated products were obtained with overall inversion of configuration. Inversion is proposed to occur during oxidative addition of C to form Pd(IV) intermediate D.