Oelke, Alexander J. and Sun, Jianwei and Fu, Gregory C. (2012) Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group. Journal of the American Chemical Society, 134 (6). pp. 2966-2969. ISSN 0002-7863. PMCID PMC3288265. doi:10.1021/ja300031w. https://resolver.caltech.edu/CaltechAUTHORS:20200428-095145561
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Abstract
To date, effective nickel-catalyzed enantioselective cross-couplings of alkyl electrophiles that bear oxygen leaving groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents. In this Communication, we establish that, in the presence of a nickel/pybox catalyst, a variety of racemic propargylic carbonates are suitable partners for asymmetric couplings with organozinc reagents. The method is compatible with an array of functional groups and utilizes commercially available catalyst components. The development of a versatile nickel-catalyzed enantioselective cross-coupling process for electrophiles that bear a leaving group other than a halide adds a significant new dimension to the scope of these reactions.
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| Additional Information: | © 2012 American Chemical Society. Received: January 2, 2012. Published: February 1, 2012. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM62871) and the Alexander von Humboldt Foundation (research fellowship for A.J.O.). We thank Dr. Wataru Muramatsu for a preliminary investigation. The authors declare no competing financial interest. | |||||||||
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| Issue or Number: | 6 | |||||||||
| PubMed Central ID: | PMC3288265 | |||||||||
| DOI: | 10.1021/ja300031w | |||||||||
| Record Number: | CaltechAUTHORS:20200428-095145561 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20200428-095145561 | |||||||||
| Official Citation: | Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group Alexander J. Oelke, Jianwei Sun, and Gregory C. Fu Journal of the American Chemical Society 2012 134 (6), 2966-2969 DOI: 10.1021/ja300031w | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 102851 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | George Porter | |||||||||
| Deposited On: | 29 Apr 2020 14:14 | |||||||||
| Last Modified: | 16 Nov 2021 18:16 |
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