Premium
The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α‐Difluoro‐β‐amino Amides
Author(s) -
Zhang Rui,
Zhang Zhikun,
Zhou Qi,
Yu Lefei,
Wang Jianbo
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901591
Subject(s) - difluorocarbene , imine , cycloaddition , chemistry , isocyanide , amino acid , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , biochemistry
Fluorine‐containing β‐amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the reaction of difluorocarbene and isocyanide, which further undergoes [2+2] cycloaddition with imine. The three‐component reaction affords α,α‐difluoro‐β‐amino amides in good yields. Mechanistic studies reveal the unique properties of the difluoroketenimine in the [2+2] cycloaddition with imine.