Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines

Eunae Kim, Hyun Ji Jeon, Sehoon Park*, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Described herein is an organoborane-catalysed consecutive borylative reduction of quinolines and isoquinolines to furnish tetrahydro(iso)quinolines bearing a C(sp3)−B bond β to the nitrogen atom. The installed C−B bond is oxidatively transformed to the hydroxy group in one pot. The present double hydroboration is proposed to proceed via a stepwise ionic mechanism involving a boronium ion. The stereo-outcome was found to be dependent on the position (C2 vs C4) of the substituents in quinolines. (Figure presented.).

Original languageEnglish
Pages (from-to)308-313
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number2
DOIs
StatePublished - 23 Jan 2020
Externally publishedYes

Keywords

  • Lewis acidic borane
  • consecutive reaction
  • diastereoselectivity
  • hydroboration
  • ionic mechanism

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