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

• Kubota, Koji

• Watanabe, Yuta

• Ito, Hajime

抄録

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.

収録刊行物

• Advanced synthesis & catalysis

  Advanced synthesis & catalysis 358 (15), 2379-2384, 2016-07-29

  Wiley-Blackwell

キーワード

• asymmetric catalysis
• boron
• copper
• synthetic methods

詳細情報

• CRID: 1050001339021617024
• NII論文ID: 120006331853
• HANDLE: 2115/66982
• ISSN: 16154150
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles