Synthesis of medicinally relevant oxalylamines via copper/Lewis acid synergistic catalysis.

2021 
Allylamines have long been recognized as valuable synthons because of their excellent reactivity in organic synthesis. Here, 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.
    • Correction
    • Source
    • Cite
    • Save
    55
    References
    0
    Citations
    NaN
    KQI
    []