Synthesis of Functionalized Pyridine‐2,6‐bis(imidazolines) by Ring Transformation of 4‐(Aminomethyl)oxazoline Derivatives

Schulz, Marvin; Christoffers, Jens

doi:10.1002/ejoc.201301204

Cited by 5 publications

(1 citation statement)

References 38 publications

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“…As highlighted in entries 4–6 in Table , pyBOX ligands ( L4 – L6 ) with varied steric environments were evaluated for the model reaction, and generally, moderate yields (59–71%) and improved enantiocontrol were observed. To our surprise, a sharp increase of both efficiency and ee value of the reaction was observed when chiral hydroxyl-containing pyBOX ligand L7 was employed (Table , entry 7:94% yield and 60% ee), which was nicely developed by Iwasa and co-workers . The reaction performed at a lower temperature provided a slightly improved result with a prolonged time (Table , entry 8:97% yield and 65% ee).…”

Section: Results and Discussionmentioning

confidence: 68%

Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions

Zhang

Yao

et al. 2017

J. Am. Chem. Soc.

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The Wittig reaction, which produces alkenes from phosphorus ylides (P-ylides) and carbonyls, is one of the most powerful tools in chemical synthesis. This Nobel Prize-winning reaction is widely used in natural product synthesis, fine chemical production (i.e., medicines and agricultural agents), and polymer functionalization. Despite these great achievements, the potential of the Wittig reaction, particularly regarding the access of chiral alkene building blocks, has not been fully exploited. The main area that requires additional exploration is the development of general and practical methods to efficiently prepare chiral P-ylides. Here, we show that highly functionalized chiral P-ylides can be easily synthesized through a copper-catalyzed asymmetric propargylic alkylation reaction from phosphonium salts and racemic propargylic esters. The subsequent Wittig reactions enable the synthesis of versatile alkene building blocks, chiral α-propargylic acrylates, and α-propargylic allenoates, with a wide substrate scope and satisfactory functional group compatibility. This transformation features inexpensive transition-metal catalysts, user-friendly conditions, easily available feedstock, and high-valued products.

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Section: Results and Discussionmentioning

confidence: 68%

Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions

Zhang

Yao

et al. 2017

J. Am. Chem. Soc.

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Bifunctional Diaminoterephthalate Fluorescent Dye as Probe for Cross‐Linking Proteins

Wallisch

Sulmann

Koch

et al. 2017

Chemistry A European J

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Diaminoterephthalates are fluorescent dyes and define scaffolds, which can be orthogonally functionalized at their two carboxylate residues with functional residues bearing task specific reactive groups. The synthesis of monofunctionalized dyes with thiol groups for surface binding, an azide for click chemistry, and a biotinoylated congener for streptavidin binding is reported. Two bifunctionalized dyes were prepared: One with an azide for click chemistry and a biotin for streptavidin binding, the other with a maleimide for reaction with thiol and a cyclooctyne moiety for ligation with copper-free click chemistry. In general, the compounds are red to orange, fluorescent materials with an absorption at about 450 nm and an emission at 560 nm with quantum yields between 2-41 %. Of particular interest is the maleimide-functionalized compound, which shows low fluorescence quantum yield (2 %) by itself. After addition of a thiol, the fluorescence is "turned on"; quantum yield 41 %.

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ChemInform Abstract: Synthesis of Functionalized Pyridine‐2,6‐bis(imidazolines) by Ring Transformation of 4‐(Aminomethyl)oxazoline Derivatives.

Schulz

Christoffers

2014

ChemInform

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Synthesis of Functionalized Pyridine‐2,6‐bis(imidazolines) by Ring Transformation of 4‐(Aminomethyl)oxazoline Derivatives

Cited by 5 publications

References 38 publications

Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions

Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions

Bifunctional Diaminoterephthalate Fluorescent Dye as Probe for Cross‐Linking Proteins

ChemInform Abstract: Synthesis of Functionalized Pyridine‐2,6‐bis(imidazolines) by Ring Transformation of 4‐(Aminomethyl)oxazoline Derivatives.

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