Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
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Fu_Nickel-catalyzed.pdf
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Author(s)
Oelke, Alexander J.
Sun, Jianwei
Fu, Gregory C.
Date Issued
February 2012
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Oelke, Alexander J., Jianwei Sun, and Gregory C. Fu. “Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group.” Journal of the American Chemical Society 134, no. 6 (February 15, 2012): 2966-2969.
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Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja300031w
