High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
KAUST Grant NumberKUS-11- 006-02
Online Publication Date2010-06-14
Print Publication Date2010-07
Permanent link to this recordhttp://hdl.handle.net/10754/598496
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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.
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.
SponsorsThis 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.
PublisherGeorg Thieme Verlag KG
PubMed Central IDPMC2976558
CollectionsPublications Acknowledging KAUST Support
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