Lou, Sha and Fu, Gregory C. (2010) Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones. Journal of the American Chemical Society, 132 (4). pp. 1264-1266. ISSN 0002-7863. PMCID PMC2814537. doi:10.1021/ja909689t. https://resolver.caltech.edu/CaltechAUTHORS:20200428-095146636
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Abstract
The first asymmetric Kumada reactions of alkyl electrophiles are described, specifically, cross-couplings of racemic α-bromoketones with aryl Grignard reagents. Several features of this investigation are of interest. First, the couplings proceed at remarkably low temperature (−40 or −60 °C), which enables the asymmetric synthesis of racemization-prone α-arylketones. Second, dialkyl ketones undergo enantioselective coupling in good ee and yield. Third, readily available bis(oxazolines) are shown for the first time to be effective ligands for cross-couplings of alkyl electrophiles, thereby opening the door to new opportunities in asymmetric catalysis.
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| Additional Information: | © 2010 American Chemical Society. Received 15 November 2009. Published online 5 January 2010. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), Merck Research Laboratories, and Novartis. We thank Pamela M. Lundin and Koyel X. Bhattacharyya for preliminary studies. | |||||||||
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| Issue or Number: | 4 | |||||||||
| PubMed Central ID: | PMC2814537 | |||||||||
| DOI: | 10.1021/ja909689t | |||||||||
| Record Number: | CaltechAUTHORS:20200428-095146636 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20200428-095146636 | |||||||||
| Official Citation: | Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones Sha Lou and Gregory C. Fu Journal of the American Chemical Society 2010 132 (4), 1264-1266 DOI: 10.1021/ja909689t | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 102862 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | George Porter | |||||||||
| Deposited On: | 30 Apr 2020 15:39 | |||||||||
| Last Modified: | 16 Nov 2021 18:16 |
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