A novel, highly enantioselective ketone alkynylation reaction mediated by chiral zinc aminoalkoxides

  • Tan L
  • Chen C
  • Tillyer R
 et al. 
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Kilogram-scale synthesis of the HIV reverse transcriptase inhibitor efavirenz was achieved by means of a highly enantioselective alkynylation of prochiral ketones 1 with alkynyllithium or alkynylmagnesium reagents in the presence of chiral zinc aminoalkoxides as mediators. With the achiral auxiliary 2,2,2-trifluoroethanol (R3=CF3CH2), the efavirenz precursor 2 (R1=H, R2=cyclopropyl) was obtained with an ee of 99.2%

Author-supplied keywords

  • Alkynylations
  • Amino alcohols
  • Ketones
  • Nucleophilic additions
  • Zinc

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  • Lushi Tan

  • Cheng Y. Chen

  • Richard D. Tillyer

  • E. J J Grabowski

  • Paul J. Reider

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