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• W2754392783 abstract "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." @default.
• W2754392783 created "2017-09-25" @default.
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• W2754392783 date "2017-11-01" @default.
• W2754392783 modified "2023-09-27" @default.
• W2754392783 title "Diastereoselectivity of cyclopropanation of substituted α-fluorostyrenes versus styrenes by different methods" @default.
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• W2754392783 doi "https://doi.org/10.1016/j.jfluchem.2017.09.008" @default.
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