1.
Org Lett
; 25(17): 3045-3048, 2023 May 05.
Article
in English
| MEDLINE
| ID: mdl-37097727
ABSTRACT
Aminoboronic acid derivatives can serve as versatile synthetic intermediates and pharmacophores but remain difficult to synthesize. Herein we report a synthesis of the ß-aminoboronic acid motif via anti-Markovnikov hydroamination of vinylboronates. This reaction benefits from the activating effect of the boronate substituent and forms novel BON-containing heterocycles, oxazaborolidine zwitterions. A computational study is included to help determine the effects of alkene boron substitution. Derivatization reactions also support the synthetic utility of the oxazaborolidine adducts.