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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
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)
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Submitter: 小澤 友
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