19967-22-7Relevant articles and documents
Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation
Fanourakis, Alexander,Paterson, Kieran J.,Phipps, Robert J.,Williams, Benjamin D.
supporting information, p. 10070 - 10076 (2021/07/21)
The enantioselective amination of C(sp3)-H bonds is a powerful synthetic transformation yet highly challenging to achieve in an intermolecular sense. We have developed a family of anionic variants of the best-in-class catalyst for Rh-catalyzed C-H amination, Rh2(esp)2, with which we have associated chiral cations derived from quaternized cinchona alkaloids. These ion-paired catalysts enable high levels of enantioselectivity to be achieved in the benzylic C-H amination of substrates bearing pendant hydroxyl groups. Additionally, the quinoline of the chiral cation appears to engage in axial ligation to the rhodium complex, providing improved yields of product versus Rh2(esp)2 and highlighting the dual role that the cation is playing. These results underline the potential of using chiral cations to control enantioselectivity in challenging transition-metal-catalyzed transformations.
Iron-catalyzed arene alkylation reactions with unactivated secondary alcohols
Jefferies, Latisha R.,Cook, Silas P.
supporting information, p. 2026 - 2029 (2014/05/06)
A simple, iron-based catalytic system allows for the inter- and intramolecular arylation of unactivated secondary alcohols. This transformation expands the substrate scope beyond the previously required activated alcohols and proceeds under mild reaction conditions, tolerating air and moisture. Furthermore, the use of an enantioenriched secondary alcohol provides an enantioenriched product for the intramolecular reaction, thereby offering a convenient approach to nonracemic products.
Synthesis of [18F] Fluoroclofilium as a potential cardiac imaging agent for PET studies
Yu,Kim,Kim,Park,Yang,Herdering,Knoechel
, p. 1151 - 1160 (2007/10/03)
N-4-(4-chlorophenyl)butyl-N,N-diethyl-7-[ 18F]fluoroheptylammonium ([18F]-fluoroclofilium) has been prepared as a potential cardiac imaging agent. For the synthesis of this radiolabelled ammonium salt, its tosyloxylated analogue was prepared as a precursor, and the non-radioactive fluorine analogue was synthesized as a reference compound. Radiofluorination was achieved by the treatment of N-4-(4-chlorophenyl)butyl-N,N-diethyl-7-(p-toluenesulfonyloxy)-heptylammonium p-toluenesulfonate with 18F- in the presence of Kryptofix-2.2.2 in acetonitrile. Copyright