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.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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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)
- Creator
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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
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:32 AM CEST
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Associated
- Ivanovs, Ilgvalds
- Bērziņa, Santa
- Lugiņina, Jevgeņija
- Belyakov, Sergey
- Rjabovs, Vitālijs
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Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids
Stereoselective Synthesis of Trisubstituted Alkenes via Intermolecular Olefin Metathesis
Stereoselective Copolymerization of Olefin with Polar Monomers to Access Stereoregular Functionalized Polyolefins
Nitro and Other Electron Withdrawing Group Activated Ruthenium Catalysts for Olefin Metathesis Reactions
Stereoselective Olefin Ring‐Opening Cross Metathesis Catalyzed by Molybdenum Imido Alkylidene N ‐Heterocyclic Carbene Complexes
Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols **
Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols **
Nitro-Grela-type complexes containing iodides – robust and selective catalysts for olefin metathesis under challenging conditions
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Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids
Stereoselective Synthesis of Trisubstituted Alkenes via Intermolecular Olefin Metathesis
Stereoselective Copolymerization of Olefin with Polar Monomers to Access Stereoregular Functionalized Polyolefins
Nitro and Other Electron Withdrawing Group Activated Ruthenium Catalysts for Olefin Metathesis Reactions
Stereoselective Olefin Ring‐Opening Cross Metathesis Catalyzed by Molybdenum Imido Alkylidene N ‐Heterocyclic Carbene Complexes
Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols **
Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols **
Nitro-Grela-type complexes containing iodides – robust and selective catalysts for olefin metathesis under challenging conditions
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