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Regio- and Stereoselective Synthesis of Multi-Alkylated Allylic Boronates through Three-Component Coupling Reactions between Allenes, Alkyl Halides, and a Diboron Reagent

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/86602

Title: Regio- and Stereoselective Synthesis of Multi-Alkylated Allylic Boronates through Three-Component Coupling Reactions between Allenes, Alkyl Halides, and a Diboron Reagent
Authors: Ozawa, Yu Browse this author
Endo, Kohei Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: Multi-substituted allylic boronates
Carboboration recation
Copper(I) catalyst
DFT calculation
Issue Date: 1-Sep-2021
Publisher: American Chemical Society
Journal Title: Journal of the American Chemical Society
Volume: 143
Issue: 34
Start Page: 13865
End Page: 13877
Publisher DOI: 10.1021/jacs.1c06538
Abstract: Multisubstituted allylic boronates are attractive and valuable precursors for the rapid and stereoselective construction of densely substituted carbon skeletons. Herein, we report the first synthetic approach for differentially 2,3,3-triallcyl-substituted allylic boronates that contain a stereodefined tetrasubstituted alkene structure. Copper(I)-catalyzed regio- and stereoselective three-component coupling reactions between gem-dialkylallenes, alkyl halides, and a diboron reagent afforded sterically congested allylic boronates. The allylboration of aldehydes diastereoselectively furnished the corresponding homoallylic alcohols that bear a quaternary carbon. A computational study revealed that the selectivity-determining mechanism was correlated to the coordination of a boryl copper(I) species to the allene substrate as well as the borylcupration step.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-QNGFNQYSKV5ZNX5JW8EP.
Type: article (author version)
URI: http://hdl.handle.net/2115/86602
Appears in Collections:総合化学院 (Graduate School of Chemical Sciences and Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 小澤 友

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