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

dc.contributor.authorStoltz, Brian
dc.contributor.authorMcDougal, Nolan
dc.contributor.authorVirgil, Scott
dc.date.accessioned2016-02-25T13:31:01Z
dc.date.available2016-02-25T13:31:01Z
dc.date.issued2010-06-14
dc.identifier.citationStoltz B, McDougal N, Virgil S (2010) High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates. Synlett 2010: 1712–1716. Available: http://dx.doi.org/10.1055/s-0030-1258094.
dc.identifier.issn0936-5214
dc.identifier.issn1437-2096
dc.identifier.pmid21072327
dc.identifier.doi10.1055/s-0030-1258094
dc.identifier.urihttp://hdl.handle.net/10754/598496
dc.description.abstractThe 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 non-polar 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.
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). 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.
dc.publisherGeorg Thieme Verlag KG
dc.subjectasymmetric catalysis
dc.subjecthigh-throughput screening
dc.subjectligands
dc.subjectpalladium
dc.subjectsolvent effect
dc.titleHigh-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
dc.typeArticle
dc.identifier.journalSynlett
dc.identifier.pmcidPMC2976558
dc.contributor.institutionThe Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
kaust.grant.numberKUS-11- 006-02
dc.date.published-online2010-06-14
dc.date.published-print2010-07


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