Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

Tomoya Miura, Junki Nakahashi, Takanori Sasatsu, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The stereoselective synthesis of anti isomers of γ-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.

Original languageEnglish
Pages (from-to)1138-1142
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number4
DOIs
Publication statusPublished - Jan 21 2019
Externally publishedYes

Keywords

  • allylation
  • allylic compounds
  • boron
  • ruthenium
  • stereoselective synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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