Open AccessMechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives
Author(s) -
Alison L Lambright,
Yanyao Liu,
Isaac A. Joyner,
Kaitlyn M. Logan,
M. Kevin Brown
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c04208
Subject(s) - chemistry , amide , cyclopentene , cyclopentane , steric effects , functional group , counterion , combinatorial chemistry , catalysis , organic chemistry , ion , polymer
A method for amide-directed Ni-catalyzed diastereoselective arylboration of cyclopentenes is disclosed. The reaction allows for the synthesis of sterically congested cyclopentane scaffolds that contain an easily derivatized boronic ester and amide functional handles. The nature of the amide directing group and its influence on the reaction outcome are investigated and ultimately reflect a predictably selective reaction based on the solvent and base counterion.