Stereoselective Michael addition of O -nucleophiles to carbohydrate-based nitro-olefin
Abstract: Michael addition reactions of O-nucleophiles to C (3) exocyclic nitromethylene derivative of diacetone glucose are reported. The reactions with primary alcohols proceed at ambient temperature in the presence of different bases with good yields and give products with excellent diastereoselectivity. The addition of the nucleophile occurs from the β-face of the carbohydrate as shown by single crystal X-ray analysis. The reactions with secondary alcohols give low yields of products while phenolic compounds do not react. Under certain conditions, isomerization of starting material is observed.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Stereoselective Michael addition of O -nucleophiles to carbohydrate-based nitro-olefin ; volume:22 ; number:2 ; year:2016 ; pages:95-98 ; extent:4
Heterocyclic communications ; 22, Heft 2 (2016), 95-98 (gesamt 4)
- Urheber
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Ivanovs, Ilgvalds
Bērziņa, Santa
Lugiņina, Jevgeņija
Belyakov, Sergey
Rjabovs, Vitālijs
- DOI
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10.1515/hc-2016-0003
- URN
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urn:nbn:de:101:1-2501130635246.908885848130
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:32 MESZ
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Beteiligte
- Ivanovs, Ilgvalds
- Bērziņa, Santa
- Lugiņina, Jevgeņija
- Belyakov, Sergey
- Rjabovs, Vitālijs
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