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

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.

authors

• Xu, Shiqing

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

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

PubMed Central ID

• 34734736

Digital Object Identifier (DOI)

• 10.1021/acs.orglett.1c03510

start page

• 8984

end page

• 8988

volume

• 23

issue

• 22

URL

• http://dx.doi.org/10.1021/acs.orglett.1c03510