Diastereo- and Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols in Two Steps from Terminal Alkynes

Tomoya Miura, Naoki Oku, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

We report the highly diastereo- and enantioselective preparation of (E)-δ-boryl-substituted anti-homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)-catalyzed 1,1-diboration reaction of terminal alkynes with B2pin2 and a palladium(I)-mediated asymmetric allylation reaction of the resulting 1,1-di(boryl)alk-1-enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.

Original languageEnglish
Pages (from-to)14620-14624
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number41
DOIs
Publication statusPublished - Oct 7 2019
Externally publishedYes

Keywords

  • allylation
  • asymmetric catalysis
  • double-bond transposition
  • homoallylic compounds
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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