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Enantioselective Pd(II)-Catalyzed Aerobic Oxidative Amidation of Alkenes and Insights into the Role of Electronic Asymmetry in Pyridine-Oxazoline Ligands

Richard I. McDonald, Paul B. White, Adam B. Weinstein, Chun Pong Tam and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin−Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

R. I. McDonald, P. W. White, A. B. Weinstein, C. P. Tam, S. S. Stahl, Org. Lett., 2011, 13, 2830-2833.

DOI: 10.1021/ol200784y (free Supporting Information)


Abstract

Enantioselective intramolecular oxidative amidation of alkenes has been achieved using a (pyrox)Pd(II)(TFA)2 as catalyst and O2 as the stoichiometric oxidant. The reactions proceed at room temperature in very good yields and with high enantioselectivity. Catalyst-controlled stereoselective cyclization reactions are demonstrated for a number of chiral substrates.

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Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N-Heterocycles

Z. Lu, S. S. Stahl, Org. Lett., 2012, 14, 1234-1237.


Key Words

pyrrolidines, oxygen


ID: J54-Y2011-1570