Open AccessSynthesis of medicinally relevant oxalylamines via copper/Lewis acid synergistic catalysis
Author(s) -
Ziying Wu,
Miao Hu,
Yangbin Jin,
Jianxiao Li,
Wanqing Wu,
Huanfeng Jiang
Publication year - 2021
Publication title -
science advances
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.928
H-Index - 146
ISSN - 2375-2548
DOI - 10.1126/sciadv.abh4088
Subject(s) - synthon , lewis acids and bases , catalysis , combinatorial chemistry , amination , lewis acid catalysis , chemistry , surface modification , reactivity (psychology) , copper , organic chemistry , medicine , alternative medicine , pathology
Allylamines have long been recognized as valuable synthons because of their excellent reactivity in organic synthesis. Her e, an efficient amination reaction of allenyl ethers via copper/Lewis acid synergistic catalysis has been established, providing straightforward access to diverse functionalized Z -oxalylamines and E -halogenated oxalylamines in good to excellent yields with high regio- and stereoselectivities. The developed method tolerates more than 100 examples that include late-stage functionalization of bioactive molecules, and features gram-scale synthesis of oxalylamines with high turnover number (TON > 1000) under mild and simple conditions. The applicability of the protocol is further demonstrated with the construction of drug molecules.