Reeves, Corey M. and Behenna, Douglas C. and Stoltz, Brian M. (2014) Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles. Organic Letters, 16 (9). pp. 2314-2317. ISSN 1523-7060. PMCID PMC4011571. doi:10.1021/ol500355z. https://resolver.caltech.edu/CaltechAUTHORS:20140424-145313873
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Abstract
The development of (trimethylsilyl)ethyl ester protected enolates is reported. The application of this class of compounds in palladium-catalyzed asymmetric allylic alkylation is explored, yielding a variety of α-quaternary six- and seven-membered ketones and lactams. Independent coupling partner synthesis engenders enhanced allyl substrate scope relative to traditional β-ketoester substrates; highly functionalized α-quaternary ketones generated by the union of (trimethylsilyl)ethyl β-ketoesters and sensitive allylic alkylation coupling partners serve to demonstrate the utility of this method for complex fragment coupling.
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| Additional Information: | © 2014 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Received: February 3, 2014; Publication Date (Web): April 11, 2014. The authors declare no competing financial interest. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. C.M.R. thanks the Rose Hills Foundation for a predoctoral fellowship. The authors thank Scott Virgil (Caltech) for helpful discussions and instrumentation assistance. Rob Craig (Caltech) and Dr. Allen Hong (Caltech) are thanked for helpful discussion. | |||||||||||||||
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| Issue or Number: | 9 | |||||||||||||||
| PubMed Central ID: | PMC4011571 | |||||||||||||||
| DOI: | 10.1021/ol500355z | |||||||||||||||
| Record Number: | CaltechAUTHORS:20140424-145313873 | |||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20140424-145313873 | |||||||||||||||
| Official Citation: | Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles Corey M. Reeves, Douglas C. Behenna, and Brian M. Stoltz Organic Letters 2014 16 (9), 2314-2317 | |||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||||||||
| ID Code: | 45195 | |||||||||||||||
| Collection: | CaltechAUTHORS | |||||||||||||||
| Deposited By: | Aucoeur Ngo | |||||||||||||||
| Deposited On: | 25 Apr 2014 16:24 | |||||||||||||||
| Last Modified: | 10 Nov 2021 17:01 |
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