Categories: C-F Bond Formation >
Synthesis of 1,2-fluoroamines
Recent Literature
In situ generation of amine-HF reagents from benzoyl fluoride and a
non-nucleophilic alcohol in the presence of a Lewis base catalyst enables the
hydrofluorination of aziridines to provide β-fluoroamines. This protocol
displays a broad scope with respect to aziridine substitution and N-protecting
groups. Regio- and diastereoselective ring opening to access medicinally
relevant β-fluoroamine building blocks are presented.
J. A. Kalow, D. E. Schmitt, A. G. Doyle, J. Org. Chem., 2012,
77, 4177-4183.
The charge density of fluoride with a hydrogen-bond donor urea catalyst
directly influences the kinetic regioselectivity in the fluorination of
dissymmetric aziridinium salts with aryl and ester substituents. These findings
offer a route to access enantioenriched fluoroamine regioisomers from a single
chloroamine precursor.
M. A. Horwitz, A. B. Dürr, K. Afratis, Z. Chen, J. Soika, K. E. Christensen,
M. Fushimi, R. S. Paton, V. Gouverneur, J. Am. Chem. Soc.,
2023, 145, 9708-9717.
The charge density of fluoride with a hydrogen-bond donor urea catalyst
directly influences the kinetic regioselectivity in the fluorination of
dissymmetric aziridinium salts with aryl and ester substituents. These findings
offer a route to access enantioenriched fluoroamine regioisomers from a single
chloroamine precursor.
M. A. Horwitz, A. B. Dürr, K. Afratis, Z. Chen, J. Soika, K. E. Christensen,
M. Fushimi, R. S. Paton, V. Gouverneur, J. Am. Chem. Soc.,
2023, 145, 9708-9717.
A dianionic
phase-transfer catalyst enables an asymmetric fluorofunctionalization of γ,γ-disubstituted allylamine
derivatives. Depending on the substituents on the alkene moiety, the
reaction afforded chiral allylic fluorides and fluorinated dihydrooxazines in a
highly enantioselective manner.
T. Niwa, K. Nishibashi, H. Sato, K. Ujiie, K. Yamashita, H. Egami, Y.
Hamashima, J. Am. Chem. Soc.,
2021, 143, 16599-16609.
Related
A nickel-catalyzed enantioselective hydrofluoromethylation of enamides and
enol esters with ICH2F as the fluoromethyl source provides chiral
α-fluoromethylated amides as well as esters with wide functional group
compatibility as well as excellent enantioselectivity.
Y. Du, S. Chen, H. Cao, Y. Zhang, H. Lei, G. Xia, H. Huang, Z. Li, Org. Lett., 2023, 25,
2218-2222.