Asymmetric Carbon-Carbon Bond Formation gamma to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes

Author(s)
Smith, Sean W.; Fu, Gregory C.
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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.
Date issued
2009-09
URI
http://hdl.handle.net/1721.1/67692
Department
Massachusetts Institute of Technology. Department of Chemistry
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
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