High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
KAUST Grant NumberKUS-11- 006-02
Permanent link to this recordhttp://hdl.handle.net/10754/598496
MetadataShow full item record
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.
PublisherThieme Publishing Group
PubMed Central IDPMC2976558
CollectionsPublications Acknowledging KAUST Support
- Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates.
- Authors: Trost BM, Xu J, Schmidt T
- Issue date: 2009 Dec 30
- Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.
- Authors: Behenna DC, Mohr JT, Sherden NH, Marinescu SC, Harned AM, Tani K, Seto M, Ma S, Novák Z, Krout MR, McFadden RM, Roizen JL, Enquist JA Jr, White DE, Levine SR, Petrova KV, Iwashita A, Virgil SC, Stoltz BM
- Issue date: 2011 Dec 9
- Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre via the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates.
- Authors: Kondo H, Maeno M, Hirano K, Shibata N
- Issue date: 2018 May 29
- Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates.
- Authors: Alexy EJ, Zhang H, Stoltz BM
- Issue date: 2018 Aug 15
- Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents.
- Authors: Trost BM, Lehr K, Michaelis DJ, Xu J, Buckl AK
- Issue date: 2010 Jul 7