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Synfacts 2011(10): 1089-1089  
DOI: 10.1055/s-0030-1261128
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Pd(II)-Catalyzed Aerobic Oxidative Amidation of Alkenes

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
R. I. McDonald, P. B. White, A. B. Weinstein, C. P. Tam, S. S. Stahl*
University of Wisconsin - Madison, USA
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Publication History

Publication Date:
20 September 2011 (online)

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Significance

In this study the authors developed highly enantioselective Wacker-type oxidative cyclizations of δ,ε-unsaturated sulfonamides using Pd(pyrox)(TFA)2 as catalyst and dioxygen as the only stoichiometric oxidant. Good to excellent yields (58-98%) and high enantioselectivities (92-98% ee) were achieved. DFT-calculated relative free energies for the diastereomeric transition states matched the experimental results remarkably well; the synergy between the electronic asymmetry of the pyrox ligand and the steric effect of the oxazoline substituent was concluded.