2024-03-29T01:43:06Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/802242022-11-17T02:08:08Zhdl_2115_20045hdl_2115_139Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of PyrrolesHayama, KeiichiKojima, RyotoKubota, Koji1000090282300Ito, Hajimeopen accessThis 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.9b04581.500The 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.American Chemical Society2020-01-17engjournal articleAMhttp://hdl.handle.net/2115/80224https://doi.org/10.1021/acs.orglett.9b045811523-7060Organic letters222739744https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/80224/1/Org.%20Lett.%2022%282%29.pdfapplication/pdf520.79 KB2020-01-17