809282-90-4Relevant academic research and scientific papers
Diastereoselectivity of cyclopropanation of substituted α-fluorostyrenes versus styrenes by different methods
Bartels, Katharina,Schinor, Benjamin,Haufe, Günter
, p. 200 - 205 (2017/10/13)
The diastereoselectivity of cyclopropanations of styrene and α-fluorostyrene with diazoacetate depends on the catalyst used and the presence or absence of the fluorine substituent. The Cu(acac)2 catalyzed reaction of styrene with diazoacetate led to 3:1 selectivity in favor of trans-2-phenylcyclopropane carboxylate, while α-fluorostyrene gave a 1:1 mixture of cis/trans-isomers. A competition experiment proved that α-fluorostyrene reacted slower compared to styrene itself. With the bulkier tetraphenyl-iron(III)-porphyrin chloride as catalyst, 10:1 or 3:1 mixture, respectively, were obtained. An advantage of the latter protocol is the in situ formation of ethyl diazoacetate from ethyl glycinate hydrochloride in aqueous solution by diazotation avoiding the in-substance application of the potentially explosive ethyl diazoacetate. Accordingly, a series of diastereoisomeric ethyl 2-aryl-2-fluoro-cyclopropane carboxylates was synthesized from p- or m-substituted α-fluorostyrenes.
MONOAMINE OXIDASE INHIBITORS
-
Page/Page column 41-42, (2008/06/13)
The invention includes compounds of formula (I), pharmaceutically acceptable salts thereof, compositions containing compounds of formula (I), methods of inhibiting at least one monoamine oxidase using a compound of formula (I), and methods of inhibiting o
Fluorinated phenylcyclopropylamines. 2. Effects of aromatic ring substitution and of absolute configuration on inhibition of microbial tyramine oxidase
Rosen, Thomas C.,Yoshida, Shinichi,Fr?hlich, Roland,Kirk, Kenneth L.,Haufe, Günter
, p. 5860 - 5871 (2007/10/03)
A series of para-substituted diastereopure cis- and trans-2-fluoro-2- arylcyclopropylamines were synthesized and these were investigated as inhibitors of microbial tyramine oxidase from Arthrobacter sp. All compounds were shown to be competitive inhibitor
