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Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis

Liu, Wen-Bo and Reeves, Corey M. and Virgil, Scott C. and Stoltz, Brian M. (2013) Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis. Journal of the American Chemical Society, 135 (29). pp. 10626-10629. ISSN 0002-7863. PMCID PMC3756902. https://resolver.caltech.edu/CaltechAUTHORS:20131002-102340513

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Abstract

Highly congested vicinal stereocenters comprised of tertiary and all-carbon quaternary centers were generated via Ir-catalyzed asymmetric allylic alkylation of β-ketoesters. These catalytic reactions proceed in excellent yields with a broad scope on either reaction partner and with outstanding regio-, diastereo-, and enantiocontrol. Implementation of a subsequent Pd-catalyzed alkylation affords dialkylated products with pinpoint stereochemical control of both chiral centers.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja4052075 DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja4052075PublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3756902/PubMed CentralArticle
ORCID:
AuthorORCID
Liu, Wen-Bo0000-0003-2687-557X
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 American Chemical Society. Received: May 23, 2013; Published: July 7, 2013. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. Shanghai Institute of Organic Chemistry (SIOC) is thanked for a postdoctoral fellowship to W.-B.L. Dr. Mona Shahgholi and Naseem Torian are acknowledged for mass spectrometry assistance. Lawrence Henling is acknowledged for X-ray crystallographic structural determination. The authors thank Mr. Jeff Holder for the preparation of [Ir(cod)Cl]2. The authors are thankful to Professor Shu-Li You and Mr. Robert Craig for L3 and (R)-L8, respectively, and for helpful discussions.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
Issue or Number:29
PubMed Central ID:PMC3756902
Record Number:CaltechAUTHORS:20131002-102340513
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20131002-102340513
Official Citation:Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis Wen-Bo Liu, Corey M. Reeves, Scott C. Virgil, and Brian M. Stoltz Journal of the American Chemical Society 2013 135 (29), 10626-10629
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:41606
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:02 Oct 2013 21:28
Last Modified:09 Mar 2020 13:19

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