Stereo- and Enantioselective Synthesis of Propionate-Derived Trisubstituted Alkene Motifs

Tomoya Miura, Naoki Oku, Yota Shiratori, Yuuya Nagata, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

We report a new method for constructing propionate-derived trisubstituted alkene motifs in a stereoselective manner. 1-Substituted 1,1-di(pinacolatoboryl)-(E)-alk-2-enes are generated in situ from 1-substituted 1,1-di(pinacolatoboryl)alk-3-enes through ruthenium(II)-catalyzed double-bond transposition. These species undergo a chiral phosphoric acid catalyzed allylation reaction of aldehydes to produce the E isomers of anti-homoallylic alcohols. On the other hand, the corresponding Z isomers of anti-homoallylic alcohols are obtained when a dimeric palladium(I) complex is employed as the catalyst for this double-bond transposition. Thus, both E and Z isomers can be synthesized from the same starting materials. A B−C(sp2) bond remaining with the allylation product undergoes the Suzuki–Miyaura cross-coupling reaction to furnish a propionate-derived trisubstituted alkene motif in a stereo-defined form. The present method to construct the motifs with (E)- and (Z)-alkenes are successfully applied to the syntheses of (+)-isotrichostatic acid, (−)-isotrichostatin RK, and (+)-trichostatic acid, respectively.

Original languageEnglish
Pages (from-to)3861-3868
Number of pages8
JournalChemistry - A European Journal
Volume27
Issue number11
DOIs
Publication statusPublished - Feb 19 2021
Externally publishedYes

Keywords

  • allylation
  • asymmetric synthesis
  • palladium
  • propionate-derived substructure
  • ruthenium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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