Chang Xu, R. Cheng, Yun‐Cheng Luo
Jul 8, 2020
Citations
0
Influential Citations
40
Citations
Journal
Angewandte Chemie
Abstract
2-Pyrroline and 2-azetine are useful synthons for the synthesis of pyrrolidines and azetidines that widely exist in natural products, pharmaceuticals, and agrochemicals. But efficient methods for dicarbofuntionalization of these cyclic alkenes are limited. Particularly, the dicarbofunctionalization of endocyclic enecarbamates to achieve fluorinated compounds remains an unsolved issue, despite of the wide applications of organofluorinated molecules in life and materials science. Here, we report a nickel-catalyzed trans -selective dicarbofunctionalization of N -Boc-2-pyrroline and N -Boc-2-azetine, a class of endocyclic enecarbamates previously unexplored by transition-metal catalyzed dicarbofunctionalization. The reaction can also extend to six and seven membered endocyclic enamides. A variety of arylzinc reagents and bromodifluoroacetate and its derivatives are applicable to the reaction, providing a straightforward and efficient access to an array of pyrrolidine- and azetidine-containing fluorinated amino acids and oligopeptides, which may have applications in life science. Specifically, this protocol paves a new way to the efficient synthesis of functionalized azetidines that are of great interest in pharmacological studies.