Catalyst‐Free Aldol Additions of 1,3‐Dicarbonyl Compounds

Rohr, Kerstin; Mahrwald, Rainer

doi:10.1002/adsc.200800554

Cited by 34 publications

(16 citation statements)

References 28 publications

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“…36 First, they started their experiment using L-proline as an organocatalyst and ethyl glyoxylate (43) and ethyl acetoacetate (44) as the model substrates. In this case, higher amounts of aldol adducts were observed in the reaction mixture.…”

Section: Aldol Additions Of 13-dicarbonyl Compoundsmentioning

confidence: 99%

A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability

Sarkar

Santra

Kundu³

et al. 2016

Green Chem.

197

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The keen success has been achieved towards the synthesis of new product and process as the twelve principle of "Green Chemistry" was formulated in 1990s. These products and processes are more compatible with human health, society and the environment. In this review a collection of researches has been documented from the view point of green chemistry. The main theme of this review is neat reactions which are solvent and catalyst-free reactions. Neat reactions in absence of any solvents and catalysts with the concise forms of microwaves, ball milling neat reactions have been described.

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Section: Aldol Additions Of 13-dicarbonyl Compoundsmentioning

confidence: 99%

A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability

Sarkar

Santra

Kundu³

et al. 2016

Green Chem.

197

View full text Add to dashboard Cite

show abstract

“…[1] Very recently Mahrwald described a catalyst-free aldol addition of several 1,3-dicarbonyl compounds to activated aldehydes like ethyl glyoxylate in good to high yields. [8] Even if this can be considered the most effective procedure ever reported, aromatic aldehydes were completely unreactive while inactivated aliphatic aldehydes were not tested. [8] In the past years several methods have been tried but even under very mild conditions (i.e., in the presence of weak base or weak acid or in a mixture of both, in proline-organocatalyzed conditions, etc.…”

Section: Introductionmentioning

confidence: 98%

“…[8] Even if this can be considered the most effective procedure ever reported, aromatic aldehydes were completely unreactive while inactivated aliphatic aldehydes were not tested. [8] In the past years several methods have been tried but even under very mild conditions (i.e., in the presence of weak base or weak acid or in a mixture of both, in proline-organocatalyzed conditions, etc. ), variable mixtures of regioisomers, dehydration products and aldol adducts have been observed.…”

Section: Introductionmentioning

confidence: 98%

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Trimethylchlorosilane and Silicon Tetrachloride in Two Novel Methodologies for the Efficient and Mild Aldol Addition of β‐Keto Esters and Malonates to Aldehydes

Massa¹,

Roscigno²,

Caprariis³

et al. 2010

Adv Synth Catal

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Efficient and mild aldol additions of bketo esters and malonates to aldehydes are described using two novel protocols in the presence of silicon tetrachloride and trimethylchlorosilane, respectively. Scope and limitations of the methods have been discussed. Moreover the stability of the obtained products, trimethylsilyl protection of the hydroxy group, as well as the role of both silicon tetrachloride and trimethylchlorosilane in attaining the final products have been analyzed.

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“…The starting point of this study were observations that have been made in aldol additions of aldehydes with 1.3-dicarbonyl compounds [134]. These reactions proceed without any reagent or catalyst.…”

mentioning

confidence: 99%

Organocatalyzed Cascade Reaction in Carbohydrate Chemistry

Mahrwald

2015

SpringerBriefs in Molecular Science

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The extensive and extremely strong development of organocatalysis over the last years provided versatile methodologies for convenient utilization of the carbonyl function of unprotected carbohydrates in C-C-bond formation processes. These biomimetic amine-activated mechanisms enable multiple cascade-protocols for the synthesis of a large scope of carbohydrate derived compound classes. Several, only slightly different protocols have been developed for the application of 1.3-dicarbonyls in stereoselective chain-elongation of unprotected carbohydrates and the synthesis of highly functionalized C-glycosides of defined configuration. Furthermore, the latter class of compounds can also be accessed by the use of methyl ketones. So a high substrate scope is available for the installation of desired functionalities in C-glycosides. By a one-pot, operationally simple cascade reaction of isocyanides with unprotected aldoses and amino acids an access to a broad range of defined glycosylated pseudopeptides is given. The elaborated organocatalyzed cascade-reactions provide defined access to highly functionalized carbohydrate derivatives. Depending on the reaction conditions different origin to control the installation of configuration during the bond-formation process were observed. The demonstrated organocatalyzed cascade sequences indicate the great potential of unprotected carbohydrates in the synthesis of highly functionalized bio-mimetic structure motifs by operationally simple, one-pot protocols.Due to the great biological importance of carbon chain elongated carbohydrates, the synthesis of this structural diverse compound class has attracted high synthetic interest from the scientific community. Among the elongated carbohydrates, C-Glycosides have gained considerable importance over the last few decades, since they are configuratively stable under enzymatic conditions and less prone to cleavage at the anomeric carbon. As such they are appealing substrates for chemical biology and medicinal chemistry.

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Catalyst‐Free Aldol Additions of 1,3‐Dicarbonyl Compounds

Cited by 34 publications

References 28 publications

A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability

A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability

Trimethylchlorosilane and Silicon Tetrachloride in Two Novel Methodologies for the Efficient and Mild Aldol Addition of β‐Keto Esters and Malonates to Aldehydes

Organocatalyzed Cascade Reaction in Carbohydrate Chemistry

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