Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes
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Author(s)
Smith, Sean W.
Fu, Gregory C.
Date Issued
September 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Smith, Sean W., and Gregory C. Fu. “Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes.” Journal of the American Chemical Society 131.40 (2009): 14231-14233.
Version
Author's final manuscript
Abstract
A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ functionalization of carbonyl (and related) compounds.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/ja9061823
