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  • Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction.
  • Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction. (en)
Title
  • Model synthesis of six-membered carbocyclic spironucleosides
  • Model synthesis of six-membered carbocyclic spironucleosides (en)
skos:prefLabel
  • Model synthesis of six-membered carbocyclic spironucleosides
  • Model synthesis of six-membered carbocyclic spironucleosides (en)
skos:notation
  • RIV/61388963:_____/10:00351445!RIV11-MSM-61388963
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(1M0508), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika
  • 12
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 271830
http://linked.open...ai/riv/idVysledku
  • RIV/61388963:_____/10:00351445
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • spironucleosides; carbocyclic; Bucherer-Bergs reaction; Michaels addition; tandem reaction (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • CZ - Česká republika
http://linked.open...ontrolniKodProRIV
  • [F6B4240810EA]
http://linked.open...i/riv/nazevZdroje
  • Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 75
http://linked.open...iv/tvurceVysledku
  • Dračínský, Martin
  • Hřebabecký, Hubert
  • Nencka, Radim
http://linked.open...ain/vavai/riv/wos
  • 000285770100004
http://linked.open...n/vavai/riv/zamer
issn
  • 0010-0765
number of pages
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