Synthesis and stereochemistry of fluorinated and non-fluorinated 4-alkoxycarbonyl-2-vinyldiazocarbonyl compounds

Murat B. Supurgibekov, G.K.Surya Prakash, Valerij A.Nikolaev.

Research output

Abstract

Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and transvinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyldouble bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonylcompounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16–37%. An approach via diazo transfer followed by the Wittig reaction,in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37–69%). The configuration of the resulting F- and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.
Original languageEnglish
Pages (from-to)1215–1226
JournalSynthesis
Volume45
Issue number9
DOIs
Publication statusPublished - 2013

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