open access

https://hdl.handle.net/2115/80224

Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of Pyrroles

英語

2020-01-17

American Chemical Society

Organic letters

22(2)

739-744

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.

学術雑誌論文

Accepted Manuscript

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.

1523-7060