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

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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 beta 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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2020-01
Language
English
Article Type
Article
Citation

ADVANCED SYNTHESIS & CATALYSIS, v.362, no.2, pp.308 - 313

ISSN
1615-4150
DOI
10.1002/adsc.201901050
URI
http://hdl.handle.net/10203/274193
Appears in Collection
CH-Journal Papers(저널논문)
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