Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters

Handle URI:
http://hdl.handle.net/10754/599132
Title:
Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters
Authors:
Kikushima, Kotaro; Holder, Jeffrey C.; Gatti, Michele; Stoltz, Brian M.
Abstract:
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF(3))(2) and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.
Citation:
Kikushima K, Holder JC, Gatti M, Stoltz BM (2011) Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters. Journal of the American Chemical Society 133: 6902–6905. Available: http://dx.doi.org/10.1021/ja200664x.
Publisher:
American Chemical Society (ACS)
Journal:
Journal of the American Chemical Society
KAUST Grant Number:
KUS-11-006-02
Issue Date:
11-May-2011
DOI:
10.1021/ja200664x
PubMed ID:
21495647
PubMed Central ID:
PMC3087848
Type:
Article
ISSN:
0002-7863; 1520-5126
Sponsors:
This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. K.K. acknowledges the Japan Society for the Promotion of Science for a postdoctoral fellowship. M.G. is grateful to the Swiss National Science Foundation for financial support through a postdoctoral fellowship.
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Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorKikushima, Kotaroen
dc.contributor.authorHolder, Jeffrey C.en
dc.contributor.authorGatti, Micheleen
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T13:53:28Zen
dc.date.available2016-02-25T13:53:28Zen
dc.date.issued2011-05-11en
dc.identifier.citationKikushima K, Holder JC, Gatti M, Stoltz BM (2011) Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters. Journal of the American Chemical Society 133: 6902–6905. Available: http://dx.doi.org/10.1021/ja200664x.en
dc.identifier.issn0002-7863en
dc.identifier.issn1520-5126en
dc.identifier.pmid21495647en
dc.identifier.doi10.1021/ja200664xen
dc.identifier.urihttp://hdl.handle.net/10754/599132en
dc.description.abstractThe first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF(3))(2) and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.en
dc.description.sponsorshipThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. K.K. acknowledges the Japan Society for the Promotion of Science for a postdoctoral fellowship. M.G. is grateful to the Swiss National Science Foundation for financial support through a postdoctoral fellowship.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titlePalladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocentersen
dc.typeArticleen
dc.identifier.journalJournal of the American Chemical Societyen
dc.identifier.pmcidPMC3087848en
dc.contributor.institutionThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.en
kaust.grant.numberKUS-11-006-02en

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