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Published November 13, 2013 | Supplemental Material
Journal Article Open

Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution


A palladium-catalyzed, atroposelective C−P coupling process has been developed for the asymmetric synthesis of QUINAP and its derivatives in high enantiomeric excess. Bromide, triflate (OTf) and 4-methanesulfonylbenzenesulfonate (OSs) precursors were studied, leading in the case of the triflate to a novel dynamic kinetic resolution involving isomerization of an arylpalladium intermediate. The operationally simple methods described in this communication afford these important ligands in good to high yields and selectivity using low catalyst loading (≤3 mol % Pd).

Additional Information

© 2013 American Chemical Society. Published In Issue November 13, 2013. Article ASAP November 04, 2013. Just Accepted Manuscript October 23, 2013. Received: September 12, 2013. We thank the Gordon and Betty Moore Foundation and Caltech for financial support and Prof. Robert H. Grubbs, Prof. Sarah E. Reisman, and Prof. Gregory C. Fu for helpful discussions. Dr. Jacob Y. Cha, Mr. Andrew D. Lim, and Mr. Boram D. Hong are acknowledged for contributing samples of 2a and 2b.

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