About: Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring     Goto   Sponge   NotDistinct   Permalink

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Description
  • 1,6-Anhydro-2,3,4-trideoxy-2,3-(tosylepimino)-β-D-hexopyranoses 1 and 2 underwent aziridine ring-opening reactions with halides and other heteroatom-centered nucleophiles. Ribo-epimine 1 provided trans-diaxial and cis products. The lyxo-epimine 2 gave trans-diaxial and trans-diequatorial products, depending upon the reaction conditions (acid cleavage versus base cleavage) and the nucleophile (hard nucleophiles versus soft ones). These results have been rationalized by assuming that both SN2 and borderline SN2 cleavage mechanisms are operative.
  • 1,6-Anhydro-2,3,4-trideoxy-2,3-(tosylepimino)-β-D-hexopyranoses 1 and 2 underwent aziridine ring-opening reactions with halides and other heteroatom-centered nucleophiles. Ribo-epimine 1 provided trans-diaxial and cis products. The lyxo-epimine 2 gave trans-diaxial and trans-diequatorial products, depending upon the reaction conditions (acid cleavage versus base cleavage) and the nucleophile (hard nucleophiles versus soft ones). These results have been rationalized by assuming that both SN2 and borderline SN2 cleavage mechanisms are operative. (en)
Title
  • Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring
  • Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring (en)
skos:prefLabel
  • Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring
  • Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring (en)
skos:notation
  • RIV/67985858:_____/09:00333114!RIV10-AV0-67985858
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(IAA400720703), P(IAA400720706), Z(AV0Z40550506), Z(AV0Z40720504), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika
  • 36
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
  • 339400
http://linked.open...ai/riv/idVysledku
  • RIV/67985858:_____/09:00333114
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • aziridines; carbohydrates; regioselectivity (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [8579C2FCBA2C]
http://linked.open...i/riv/nazevZdroje
  • European Journal of Organic Chemistry
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
  • 2009
http://linked.open...iv/tvurceVysledku
  • Buděšínský, Miloš
  • Císařová, I.
  • Sýkora, Jan
  • Karban, Jindřich
  • Kroutil, J.
http://linked.open...ain/vavai/riv/wos
  • 000273187700017
http://linked.open...n/vavai/riv/zamer
issn
  • 1434-193X
number of pages
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