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Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation Reactions
| 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)
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Submitter: 伊藤 肇
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