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High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates

McDougal, Nolan T. and Virgil, Scott C. and Stoltz, Brian M. (2010) High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates. Synlett, 2010 (11). pp. 1712-1716. ISSN 0936-5214. PMCID PMC2976558. http://resolver.caltech.edu/CaltechAUTHORS:20100713-135750673

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Abstract

The use of high-throughput screening allowed for the optimization of reaction conditions for the palladium-catalyzed asymmetric decarboxylative alkylation reaction of enolate-stabilized enol carbonates. Changing to a nonpolar reaction solvent and to an electron-deficient PHOX derivative as ligand from our standard ­reaction conditions improved the enantioselectivity for the alkylation of a ketal-protected,1,3-diketone-derived enol carbonate from 28% ee to 84% ee. Similar improvements in enantioselectivity were seen for a β-keto ester derived and an α-phenyl cyclohexanone-­derived enol carbonate.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1055/s-0030-1258094 DOIArticle
https://www.thieme-connect.de/DOI/DOI?10.1055/s-0030-1258094PublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2976558/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2010 Thieme Stuttgart. Received 7 April 2010. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11- 006-02
NIHR01GM080269-01
Abbott Laboratories UNSPECIFIED
Amgen UNSPECIFIED
Gordon and Betty Moore Foundation UNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:asymmetric catalysis; high-throughput screening; palladium; ligands; solvent effect
PubMed Central ID:PMC2976558
Record Number:CaltechAUTHORS:20100713-135750673
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20100713-135750673
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:19033
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:04 Aug 2010 19:51
Last Modified:15 Feb 2017 19:32

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