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Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of Pyrroles
| Title: | Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of Pyrroles |
| Authors: | Hayama, Keiichi Browse this author | | Kojima, Ryoto Browse this author | | Kubota, Koji Browse this author | | Ito, Hajime Browse this author →KAKEN DB |
| Issue Date: | 17-Jan-2020 |
| Publisher: | American Chemical Society |
| Journal Title: | Organic letters |
| Volume: | 22 |
| Issue: | 2 |
| Start Page: | 739 |
| End Page: | 744 |
| Publisher DOI: | 10.1021/acs.orglett.9b04581 |
| Abstract: | The first enantioselective synthesis of five-membered N-heterocyclic allylboronates has been accomplished by a C-B bond-forming dearomatization of pyrroles using a copper(I) catalyst. This reaction involves the regio- and enantioselective addition of a borylcopper(I) species to pyrrole-2-carboxylates, followed by the diastereoselective protonation of the resulting copper(I) enolate to afford pyrrolidine-type allylboronates. The products are highly attractive reagents for the rapid construction of pyrrolidine derivatives that bear five consecutive stereocenters via subsequent allylboration/oxidation processes. |
| Rights: | This document is the unedited Author's version of a Submitted Work that was subsequently accepted for publication in Organic Letters, copyright c American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.9b04581. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/80224 |
| 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: 久保田 浩司
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