5617-96-9Relevant academic research and scientific papers
CH2I2–Et3Al reagent in the cyclopropanation of 2-alkenyl amines
Ramazanov, Ilfir R.,Yaroslavova, Alsu V.,Dzhemilev, Usein M.
, p. 4024 - 4026 (2016)
An aluminum carbenoid is the efficient cyclopropanation reagent for the transformation of 2-alkenyl amines into cyclopropyl amines. The addition of iodine facilitates the cyclopropanation of poorly reactive 2-alkenyl amines.
Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines
Gaunt, Matthew J.,Miró, Javier,Reeve, Luke A.,Rodrigalvarez, Jesus
, p. 3939 - 3948 (2022/03/08)
Strained aminomethyl-cycloalkanes are a recurrent scaffold in medicinal chemistry due to their unique structural features that give rise to a range of biological properties. Here, we report a palladium-catalyzed enantioselective C(sp3)-H arylation of aminomethyl-cyclopropanes and -cyclobutanes with aryl boronic acids. A range of native tertiary alkylamine groups are able to direct C-H cleavage and forge carbon-aryl bonds on the strained cycloalkanes framework as single diastereomers and with excellent enantiomeric ratios. Central to the success of this strategy is the use of a simple N-acetyl amino acid ligand, which not only controls the enantioselectivity but also promotes γ-C-H activation of over other pathways. Computational analysis of the cyclopalladation step provides an understanding of how enantioselective C-H cleavage occurs and revealed distinct transition structures to our previous work on enantioselective desymmetrization of N-isobutyl tertiary alkylamines. This straightforward and operationally simple method simplifies the construction of functionalized aminomethyl-strained cycloalkanes, which we believe will find widespread use in academic and industrial settings relating to the synthesis of biologically active small molecules.
The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds
Ramazanov,Yaroslavova,Yaubasarov,Gil’manova,Dzhemilev
, p. 1869 - 1873 (2019/10/22)
A transition-metal-free method of cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides.
