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Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters

Lee, Chung Whan and Han, Seo-Jung and Virgil, Scott C. and Stoltz, Brian M. (2015) Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters. Tetrahedron, 71 (22). pp. 3666-3670. ISSN 0040-4020. PMCID PMC4429905. https://resolver.caltech.edu/CaltechAUTHORS:20141110-091731285

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Abstract

An improved method for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters is described. The asymmetric alkylation demonstrated was achieved up to 70% ee utilizing a copper(II) bis(phosphine) complex.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tet.2014.10.065DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040402014015166PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4429905/PubMed CentralArticle
ORCID:
AuthorORCID
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information: © 2014 Elsevier B.V. Received 30 September 2014; Received in revised form 24 October 2014; accepted 27 October 2014. The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. S.-J.H thanks Fulbright Commission (Foreign Student Program, No. 15111120) and the Ilju Foundation of Education & Culture (Pre-doctoral Research Fellowship) for financial support. Catalyst center (Caltech) is acknowledged for assistance with reaction screenings. Drs. Florian Vogt, Sandy Ma, Xiaoquing Han, and Shyam Krishnan are acknowledged for preliminary research.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Fulbright Commission15111120
Ilju Foundation of Education & CultureUNSPECIFIED
Subject Keywords:3,3-Disubstituted oxindole; Chiral bis(phosphine) ligands; Copper catalysis; Asymmetric catalysis
Issue or Number:22
PubMed Central ID:PMC4429905
Record Number:CaltechAUTHORS:20141110-091731285
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141110-091731285
Official Citation:Chung Whan Lee, Seo-Jung Han, Scott C. Virgil, Brian M. Stoltz, Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters, Tetrahedron, Volume 71, Issue 22, 3 June 2015, Pages 3666-3670, ISSN 0040-4020, http://dx.doi.org/10.1016/j.tet.2014.10.065. (http://www.sciencedirect.com/science/article/pii/S0040402014015166)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:51486
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:10 Nov 2014 21:34
Last Modified:09 Mar 2020 13:19

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