A Versatile Bis-Allylboron Reagent for the Stereoselective Synthesis of Chiral Diols

Belinda E. Hetzler, Giulio Volpin, Elisa Vignoni, Ana G. Petrovic, Gloria Proni, Chunhua T. Hu, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

Allylboron reagents are popular in synthesis owing to their versatility and the predictable stereochemical outcomes of their reactions with carbonyl compounds. Herein, we describe the synthesis of (Z,Z)-hexadienyl bis-boronate 1, a configurationally stable, crystalline, and easy to handle compound, which represents a class of bis-allylic boron reagents with heretofore untapped synthetic potential. In combination with a chiral phosphoric acid catalyst, the reagent can be employed for the enantioselective allyl transfer reaction to a variety of one-pot transformations, enabling swift access to functionalized 1,n-diols. The in situ conversion of the reagent into the corresponding bis-borinic ester allows for the direct and diastereoselective two-fold allyl transfer to aldehydes. This affords C2- or Ci-symmetric stereotetrads containing a 1,4-diol moiety for natural product synthesis. The usefulness of our method was demonstrated with a short synthesis of the lignan (±)-neo-olivil.

Original languageEnglish (US)
Pages (from-to)14276-14280
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number43
DOIs
StatePublished - Oct 22 2018

Keywords

  • allyboron
  • chiral phosphoric acid
  • natural products
  • stereospecific reactions
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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