High-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates
Type
ArticleKAUST Grant Number
KUS-11- 006-02Date
2010-06-14Permanent link to this record
http://hdl.handle.net/10754/598496
Metadata
Show full item recordAbstract
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.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.Publisher
Georg Thieme Verlag KGJournal
SynlettISSN
0936-52141437-2096
PubMed ID
21072327PubMed Central ID
PMC2976558ae974a485f413a2113503eed53cd6c53
10.1055/s-0030-1258094
Scopus Count
Collections
Publications Acknowledging KAUST SupportRelated articles
- Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted <i>N</i>-acyl indole-derived enol carbonates.
- Authors: Alexy EJ, Fulton TJ, Zhang H, Stoltz BM
- Issue date: 2019 Jun 21
- 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