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

Handle URI:
http://hdl.handle.net/10754/598496
Title:
High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
Authors:
Stoltz, Brian; McDougal, Nolan; Virgil, Scott
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 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.
Citation:
Stoltz 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.
Publisher:
Thieme Publishing Group
Journal:
Synlett
KAUST Grant Number:
KUS-11- 006-02
Issue Date:
14-Jun-2010
DOI:
10.1055/s-0030-1258094
PubMed ID:
21072327
PubMed Central ID:
PMC2976558
Type:
Article
ISSN:
0936-5214; 1437-2096
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). 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.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorStoltz, Brianen
dc.contributor.authorMcDougal, Nolanen
dc.contributor.authorVirgil, Scotten
dc.date.accessioned2016-02-25T13:31:01Zen
dc.date.available2016-02-25T13:31:01Zen
dc.date.issued2010-06-14en
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.en
dc.identifier.issn0936-5214en
dc.identifier.issn1437-2096en
dc.identifier.pmid21072327en
dc.identifier.doi10.1055/s-0030-1258094en
dc.identifier.urihttp://hdl.handle.net/10754/598496en
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.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). 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.en
dc.publisherThieme Publishing Groupen
dc.subjectasymmetric catalysisen
dc.subjecthigh-throughput screeningen
dc.subjectligandsen
dc.subjectpalladiumen
dc.subjectsolvent effecten
dc.titleHigh-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonatesen
dc.typeArticleen
dc.identifier.journalSynletten
dc.identifier.pmcidPMC2976558en
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.en
kaust.grant.numberKUS-11- 006-02en

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