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- Title
Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation Reactions.
- Authors
Kubota, Koji; Watanabe, Yuta; Ito, Hajime
- 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.
- Subjects
BORYLATION; QUINOLINE; COPPER; ENANTIOSELECTIVE catalysis; ENANTIOMERS
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 15, p2379
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600372