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Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation Reactions

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Title: Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation Reactions
Authors: Kubota, Koji Browse this author
Watanabe, Yuta Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: asymmetric catalysis
boron
copper
synthetic methods
Issue Date: 29-Jul-2016
Publisher: Wiley-Blackwell
Journal Title: Advanced synthesis & catalysis
Volume: 358
Issue: 15
Start Page: 2379
End Page: 2384
Publisher DOI: 10.1002/adsc.201600372
Abstract: A 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.
Rights: Advanced 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. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving (http://olabout.wiley.com/WileyCDA/Section/id-828039.html).
Type: article (author version)
URI: http://hdl.handle.net/2115/66982
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 伊藤 肇

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