Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3‐Hydroxytetrahydroquinolines. Issue 2 (30th September 2019)

• Record Type: Journal Article
• Authors: Kim, Eunae; Jeon, Hyun Ji; Park, Sehoon; Chang, Sukbok
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 308
• Page End: 313
• Publication Date: 2019-09-30
• Subjects: Lewis acidic borane -- hydroboration -- consecutive reaction -- ionic mechanism -- diastereoselectivity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901050
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :