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