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Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution

Bhat, Vikram and Wang, Su and Stoltz, Brian M. and Virgil, Scott C. (2013) Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution. Journal of the American Chemical Society, 135 (45). pp. 16829-16832. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20131108-073355250

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Abstract

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).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja409383fDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja409383fPublisherArticle
ORCID:
AuthorORCID
Bhat, Vikram0000-0001-5621-5121
Stoltz, Brian M.0000-0001-9837-1528
Virgil, Scott C.0000-0001-8586-5641
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.
Funders:
Funding AgencyGrant Number
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Issue or Number:45
Record Number:CaltechAUTHORS:20131108-073355250
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20131108-073355250
Official Citation:Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution Vikram Bhat, Su Wang, Brian M. Stoltz, and Scott C. Virgil Journal of the American Chemical Society 2013 135 (45), 16829-16832
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:42328
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:08 Nov 2013 16:52
Last Modified:09 Mar 2020 13:19

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