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Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3‐Hydroxytetrahydroquinolines
Author(s) -
Kim Eunae,
Jeon Hyun Ji,
Park Sehoon,
Chang Sukbok
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901050
Subject(s) - hydroboration , chemistry , borane , double bond , catalysis , nitrogen atom , ionic bonding , medicinal chemistry , combinatorial chemistry , stereochemistry , group (periodic table) , organic chemistry , ion
Described herein is an organoborane‐catalysed consecutive borylative reduction of quinolines and isoquinolines to furnish tetrahydro(iso)quinolines bearing a C( sp 3 )−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.