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

Eunae Kim; Hyun Ji Jeon; Sehoon Park; Sukbok Chang

doi:10.1002/adsc.201901050

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 journal › Article › peer-review

20 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 language	English
Pages (from-to)	308-313
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	362
Issue number	2
DOIs	https://doi.org/10.1002/adsc.201901050
State	Published - 23 Jan 2020
Externally published	Yes

Keywords

Lewis acidic borane
consecutive reaction
diastereoselectivity
hydroboration
ionic mechanism

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10.1002/adsc.201901050

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title = "Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines",

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.).",

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author = "Eunae Kim and Jeon, {Hyun Ji} and Sehoon Park and Sukbok Chang",

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T1 - Double Hydroboration of Quinolines via Borane Catalysis

T2 - Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines

AU - Kim, Eunae

AU - Jeon, Hyun Ji

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2020/1/23

Y1 - 2020/1/23

N2 - 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.).

AB - 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.).

KW - Lewis acidic borane

KW - consecutive reaction

KW - diastereoselectivity

KW - hydroboration

KW - ionic mechanism

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M3 - 文章

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JF - Advanced Synthesis and Catalysis

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

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