2024-03-29T10:52:29Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/669822022-11-17T02:08:08Zhdl_2115_20045hdl_2115_139Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation ReactionsKubota, KojiWatanabe, YutaIto, Hajimeasymmetric catalysisboroncoppersynthetic methods434A novel approach has been developed for the synthesis of chiral 3-boryl-tetrahydroquinolines via the copper(I)-catalyzed regio- and enantioselective protoborylation of 1,2-dihydroquinolines, which were prepared by the partial reduction of the corresponding quinoline derivatives. This dearomatization/enantioselective borylation sequence has been used to provide a facile access to a wide variety of functionalized tetrahydroquinolines under mild conditions from readily available quinoline starting materials in combination with the stereospecific transformation of a stereogenic C-B bond. A theoretical study of the mechanism for the enantioselectivity of the reaction is also described.Wiley-BlackwellJournal Articleapplication/pdfhttp://hdl.handle.net/2115/66982https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/66982/1/Ito-ASC358%2815%29.pdf1615-4150Advanced synthesis & catalysis35815237923842016-07-29enginfo:doi/10.1002/adsc.201600372Advanced synthesis & catalysis 358(15) July 28, 2016 pp.2379–2384, which has been published in final form at
http://onlinelibrary.wiley.com/doi/10.1002 adsc.201600372/abstract.
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