Chemo- and Stereoselective Dearomative Coupling of Indoles and Bielectrophilic -Imino Boronic Esters via Imine-Induced 1,2-Boronate Migration. uri icon

abstract

  • A new imine-induced 1,2-boronate migration has been developed for achieving chemo- and stereoselective dearomative coupling of C3-substituted indoles and bi-electrophilic -imino boronic esters, providing rapid access to complex chiral indoline boronic esters with four stereocenters including an all-carbon quaternary stereocenter and a tertiary -aminoboronic ester. In contrast, coupling of indoles without C3 substitution and -imino boronic esters provided tetrahydro-1H-pyrido[4,3-b]indoles via imine-induced 1,2-boronate migration followed by deborylative rearomatization.

published proceedings

  • Org Lett

altmetric score

  • 1

author list (cited authors)

  • Fu, X., Qi, Q., Xu, S., & Negishi, E.

citation count

  • 4

complete list of authors

  • Fu, Xiaoping||Qi, Qingqing||Xu, Shiqing||Negishi, Ei-Ichi

publication date

  • November 2021