期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 2, 页码 308-313出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901050
关键词
Lewis acidic borane; hydroboration; consecutive reaction; ionic mechanism; diastereoselectivity
资金
- Institute for Basic Science [IBSR010-D1]
- National Research Foundation of Korea [21A20151513223] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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.
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