Eine neue Methode zur Addition von Aldehyden an aktivierte Doppelbindungen

Stetter, Hermann; Schreckenberg, Manfred

doi:10.1002/ange.19730850208

Cited by 100 publications

(26 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[120, 121] The reaction is catalyzed by cyanide ion or a safer surrogate, the thiazolium salt, which is analogous to the biological cofactor thiamine diphosphate (TPP, 144 ). This reaction was first reported by Hermann Stetter in 1973.…”

Section: Nucleophilic Addition To C-c and C-hetero Multiple Bondsmentioning

confidence: 99%

See 1 more Smart Citation

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

2017

View full text Add to dashboard Cite

Chemical reactions that are named in honor of their true or at least perceived discoverers are known as “name reactions”. This review is a collection of biological representatives of named chemical reactions. Emphasis is placed on reaction types and catalytic mechanisms that showcase both the chemical diversity in natural product biosynthesis as well as the parallels with synthetic organic chemistry. An attempt has been made to describe the enzymatic mechanisms of catalysis within the context of their synthetic counterparts whenever possible and to discuss the mechanistic hypotheses for those reactions that are presently active areas of investigation. This review has been categorized by reaction type, e.g., condensation, nucleophilic addition, reduction and oxidation, substitution, carboxylation, radical-mediated, and rearrangements, which are subdivided by named reactions.

show abstract

Section: Nucleophilic Addition To C-c and C-hetero Multiple Bondsmentioning

confidence: 99%

“…This reaction was first reported by Hermann Stetter in 1973. [120] Under the reaction conditions, the aldehyde undergoes polarity inversion (umpolung) [122] to become a nucleophile instead of an electrophile. The mechanism of Stetter reaction is related to that of benzoin condensation.…”

Section: Nucleophilic Addition To C-c and C-hetero Multiple Bondsmentioning

confidence: 99%

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

2017

View full text Add to dashboard Cite

show abstract

“…[225] Die Synthese des Dienons 347 glich der bereits beschriebenen, wobei man von 315 ausging und den Weg über das Intermediat 346 nahm. Der Schlüsselschritt war eine intramolekulare Stetter-Reaktion [226] . [225] Schema 53.…”

Section: Angewandte Chemieunclassified

Fortschritte in der Chemie und Biologie natürlicher Antibiotika

et al. 2009

View full text Add to dashboard Cite

Seit der bahnbrechenden Entdeckung von Penicillin wurde die Vielfalt natürlich vorkommender Moleküle ausgiebig hinsichtlich ihrer Eignung als Medikamente sowie zum Auffinden neuer Leitstrukturen beim Wirkstoffdesign untersucht. Die Suche nach Wirkstoffen, mit denen Infektionskrankheiten bekämpft werden können, war dabei von besonderem Interesse und verlief sehr erfolgreich. Die Erforschung der Antibiotika weist eindrucksvolle Entdeckungen und Geschichten über die Entwicklung von Wirkstoffen auf, von denen die große Mehrheit ihren Ursprung in Naturstoffen hat. Die Chemie und besonders die chemische Synthese haben eine bedeutende Rolle dabei gespielt, natürlich vorkommende Antibiotika und deren Derivate für die medizinische Anwendung bereitzustellen, und zweifellos werden diese Disziplinen auch künftig Schlüsseltechnologien sein. In dieser Übersicht stellen wir einige der bedeutendsten neueren Entwicklungen und Fortschritte in der Chemie, Biologie und Medizin natürlich vorkommender Antibiotika vor, wobei die Totalsynthese, das Design von Analoga und die biologische Bewertung von Molekülen mit neuartigen Wirkmechanismen im Vordergrund stehen.

show abstract

“…In addition, substituents on the aromatic ring, such as Cl, Br, CH 3 O, and C 6 H 5 CH 2 O, have practically no obvious effect on the yield. However, the substrate bearing an NO 2 group on the benzene ring did not undergo any reaction under conventional conditions, but gave an abnormal product under microwave irradiation whose structure was assigned by 1 HNMR, MS and X-ray diffraction analysis ( Figure 1) to be methyl 2-(2-methyl-5-nitro-3-oxo-2,3-dihydrobenzofuran-2-yl)acetate 4. A plausible mechanism for the formation of 4 is outlined in Scheme 3.…”

mentioning

confidence: 98%

“…[1,2] The Stetter reaction is traditionally performed in protic solvents like alcohol or in aprotic ones such as DMF, dioxane, and acetonitrile. Solvent-free conditions have also been used for the Stetter reaction.…”

mentioning

confidence: 99%

An Efficient Intramolecular Stetter Reaction in Room Temperature Ionic Liquids Promoted By Microwave Irradiation

Zhou

Cao

et al. 2006

Adv Synth Catal

View full text Add to dashboard Cite

This communication describes the first report of a microwave-assisted intramolecular Stetter reaction using imidazolium-type room temperature ionic liquids (RTILs) as solvents, with thiazolium salts and Et 3 N as catalysts. The features such as good to excellent yields, shorter reaction time (5-20 min), and recyclable and reusable ionic liquid and catalyst make this method an environmentally benign and highly efficient procedure for the preparation of chromanone derivatives.

show abstract

Eine neue Methode zur Addition von Aldehyden an aktivierte Doppelbindungen

Cited by 100 publications

References 0 publications

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

Fortschritte in der Chemie und Biologie natürlicher Antibiotika

An Efficient Intramolecular Stetter Reaction in Room Temperature Ionic Liquids Promoted By Microwave Irradiation

Contact Info

Product

Resources

About