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Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors

Holder, Jeffrey C. and Marziale, Alexander N. and Gatti, Michele and Mao, Bin and Stoltz, Brian M. (2013) Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors. Chemistry: a European Journal, 19 (1). pp. 74-77. ISSN 0947-6539. PMCID PMC3753812. http://resolver.caltech.edu/CaltechAUTHORS:20130212-115138312

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Abstract

Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF_3)_2 and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/chem.201203643DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/chem.201203643/abstractPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3753812/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim. Received: September 19, 2012; Published online: December 3, 2012. The authors thank NIH-NIGMS (R01M080269–01), Caltech, Amgen, and the Deutsche Akademie der Naturforscher Leopoldina (postdoctoral fellowship A.N.M.) for financial support. J. C. H. thanks the American Chemical Society Division of Organic Chemistry for a predoctoral fellowship. M.G. is grateful to the Swiss National Science Foundation for financial support through a postdoctoral fellowship. B. M. thanks the China Scholarship Council (No.2008618001) and the University of Groningen for financial support. Anton A. Toutov is acknowledged for experimental assistance. Jinglan Zhou and Mike DeNinno (Vertex Pharmaceuticals) are acknowledged for helpful discussions and suggestions.
Funders:
Funding AgencyGrant Number
NIHR01M080269–01
CaltechUNSPECIFIED
AmgenUNSPECIFIED
Deutsche Akademie der Naturforscher LeopoldinaUNSPECIFIED
American Chemical SocietyUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
China Scholarship Council2008618001
University of GroningenUNSPECIFIED
Subject Keywords:arylboronic acids; asymmetric catalysis; conjugate addition; heterocycles; palladium
PubMed Central ID:PMC3753812
Record Number:CaltechAUTHORS:20130212-115138312
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20130212-115138312
Official Citation:Holder, J. C., Marziale, A. N., Gatti, M., Mao, B. and Stoltz, B. M. (2013), Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors. Chem. Eur. J., 19: 74–77. doi: 10.1002/chem.201203643
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:36880
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:12 Feb 2013 22:40
Last Modified:25 Jul 2017 22:11

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