Brønsted Acid Catalyzed Asymmetric Propargylation of Aldehydes

Authors

  • Pankaj Jain,

    1. Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, FL 33620 (USA)
    Search for more papers by this author
  • Hao Wang,

    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095 (USA)
    Search for more papers by this author
  • Prof. Dr. Kendall N. Houk,

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095 (USA)
    • Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095 (USA)
    Search for more papers by this author
  • Prof. Dr. Jon C. Antilla

    Corresponding author
    1. Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, FL 33620 (USA)
    • Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, FL 33620 (USA)
    Search for more papers by this author

  • We thank the National Institutes of Health (NIH GM-36700 and GM-082935) and the National Science Foundation CAREER program (NSF-0847108) for financial support.

Abstract

original image

Which gets activated? A versatile and highly enantioselective chiral Brønsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the chiral phosphoric acid activates the allenyl boronic acid pinacol ester reagent rather than the aldehyde.

Ancillary