High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
dc.contributor.author | Stoltz, Brian | |
dc.contributor.author | McDougal, Nolan | |
dc.contributor.author | Virgil, Scott | |
dc.date.accessioned | 2016-02-25T13:31:01Z | |
dc.date.available | 2016-02-25T13:31:01Z | |
dc.date.issued | 2010-06-14 | |
dc.identifier.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. | |
dc.identifier.issn | 0936-5214 | |
dc.identifier.issn | 1437-2096 | |
dc.identifier.pmid | 21072327 | |
dc.identifier.doi | 10.1055/s-0030-1258094 | |
dc.identifier.uri | http://hdl.handle.net/10754/598496 | |
dc.description.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. | |
dc.description.sponsorship | 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. | |
dc.publisher | Georg Thieme Verlag KG | |
dc.subject | asymmetric catalysis | |
dc.subject | high-throughput screening | |
dc.subject | ligands | |
dc.subject | palladium | |
dc.subject | solvent effect | |
dc.title | High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates | |
dc.type | Article | |
dc.identifier.journal | Synlett | |
dc.identifier.pmcid | PMC2976558 | |
dc.contributor.institution | The 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.number | KUS-11- 006-02 | |
dc.date.published-online | 2010-06-14 | |
dc.date.published-print | 2010-07 |