Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

Tomoya Miura, Junki Nakahashi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

(E)-δ-Boryl-substituted anti-homoallylic alcohols are synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl)alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1) palladium-catalyzed double-bond transposition of the 1,1-di(boryl)alk-3-enes to 1,1-di(boryl)alk-2-enes, 2) chiral phosphoric acid catalyzed allylation of aldehydes, and 3) palladium-catalyzed geometrical isomerization from the Z to E isomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel.

Original languageEnglish
Pages (from-to)6989-6993
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number24
DOIs
Publication statusPublished - Jun 6 2017
Externally publishedYes

Keywords

  • allylation
  • asymmetric synthesis
  • homoallylic compounds
  • organocatalysis
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid'. Together they form a unique fingerprint.

Cite this