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

Lushi Tan, Cheng Yi Chen, Richard D. Tillyer, Edward J.J. Grabowski, Paul J. Reider

Research output: Contribution to journalArticlepeer-review

198 Scopus citations

Abstract

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%.

Original languageEnglish (US)
Pages (from-to)711-713
Number of pages3
JournalAngewandte Chemie - International Edition
Volume38
Issue number5
DOIs
StatePublished - Mar 1 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

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

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