195455-97-1Relevant articles and documents
Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2
Lee, Yuseop,Choi, Jonghoon,Kim, Hyunwoo
supporting information, p. 5036 - 5039 (2018/08/24)
A divergent coupling reaction was achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A gram-scale production of Linezolid was successfully achieved.
Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations
Zhang, Yang,Zhang, Yan,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
, p. 11 - 15 (2016/05/09)
A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stere
Efficient asymmetric syntheses, determination of absolute configurations and biological activities of 1-[4,4-bis(4-fluorophenyl)butyl]-4-[2-hydroxy-3- (phenylamino)propyl]piperazine as a novel potent dopamine uptake inhibitor in the central nervous system
Kimura, Makoto,Masuda, Tomoko,Yamada, Koji,Mitani, Masaki,Kubota, Nobuo,Kawakatsu, Nobuyuki,Kishii, Kenichi,Inazu, Masato,Kiuchi, Yuji,Oguchi, Katsuji,Namiki, Takayuki
, p. 3069 - 3078 (2007/10/03)
An efficient asymmetric synthesis of the chiral N-(3-chloro-2- hydroxypropyl)anilines (2a and 2b) was achieved through the regioselective ring-opening reaction of chiral epichlorohydrin with aniline. This was applied to an asymmetric synthesis of the enantiomers of 1-[4,4-bis(4-fluorophenyl) butyl]-4-[2-hydroxy-3-(phenylamino)propyl]piperazine 1 as a novel potent dopamine uptake inhibitor. Both enantiomers as trihydrochlorides, 4a·3HCl and 4b·3HCl, could be synthesized in good total yields and optical purities of 100% ee in three steps synthesis, respectively. The absolute configurations of 4a·3HCl and 4b·3HCl were determined using the modified Mosher's method with the related compounds, the intermediates (2a and 2b) and the free bases (4a and 4b). The analytical results indicated that 4a·3HCl and 4b·3HCl have the (S)- and (R)-configuration, respectively, and a series of reactions to provide them proceeded without the apparent influence on the stereochemistry at the chiral centers. In in vitro pharmacological evaluations, 4a·3HCl and 4b·3HCl showed potent dopamine transporter binding affinities, high dopamine, moderate serotonin, and weak norepinephrine uptake inhibitory activities, and 4a·3HCl exhibited a more potent and selective dopamine uptake inhibition over the serotonin or norepinephrine uptake inhibition as compared with 4b·3HCl. An ex vivo evaluation revealed that the oral administrations of both enantiomers at a dose of 30mg/kg in rats displayed apparent dopamine uptake inhibitory activities and 4a·3HCl had a stronger tendency to inhibit dopamine uptake compared with 4b·3HCl.
