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The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis

Hong, Allen Y. and Stoltz, Brian M. (2013) The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis. European Journal of Organic Chemistry, 2013 (14). pp. 2745-2759. ISSN 1434-193X. PMCID PMC4059687. doi:10.1002/ejoc.201201761. https://resolver.caltech.edu/CaltechAUTHORS:20130620-142930731

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Abstract

All-carbon quaternary stereocenters have posed significant challenges in the synthesis of complex natural products. These important structural motifs have inspired the development of broadly applicable palladium-catalyzed asymmetric allylic alkylation reactions of unstabilized non-biased enolates for the synthesis of enantioenriched α-quaternary products. This microreview outlines key considerations in the application of palladium-catalyzed asymmetric allylic alkylation reactions and presents recent total syntheses of complex natural products that have employed these powerful transformations for the direct, catalytic, enantioselective construction of all-carbon quaternary stereocenters.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/ejoc.201201761 DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201761/abstractPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4059687/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: December 30, 2012; Published Online: March 27, 2013. The authors thank National Institutes of Health – National Institute of General Medical Sciences (grant number R01GM080269- 01), Roche, Abbott Laboratories, Amgen, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for awards and financial support. Nick O’Connor, Kelly Kim, and Christopher Haley are acknowledged for editorial assistance.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
RocheUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
AmgenUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:Total synthesis; Asymmetric catalysis; Natural products; Palladium; Allylation; All-carbon quaternary stereocenters
Issue or Number:14
PubMed Central ID:PMC4059687
DOI:10.1002/ejoc.201201761
Record Number:CaltechAUTHORS:20130620-142930731
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130620-142930731
Official Citation:Hong, A. Y. and Stoltz, B. M. (2013), The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis. Eur. J. Org. Chem., 2013: 2745–2759. doi: 10.1002/ejoc.201201761
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39005
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:21 Jun 2013 17:56
Last Modified:09 Nov 2021 23:41

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