Cathodically initiated cyclodimerization of trimethyl aconitate

Kratschmer, Silke; Schäfer, Hans J.; Fröhlich, Roland

doi:10.1016/s0022-0728(01)00470-3

Cited by 13 publications

(11 citation statements)

References 18 publications

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“…,5]oxadiazol-4-yl)-1,3-propanediamine (NBD-N3) were prepared according to Danilovtseva et al (2013). Trimethyl aconitate was synthesized according to Kratschmera et al (2001). Synthesis of model compounds is presented in Appendix S1 in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

The Probable Mechanism for Silicon Capture by Diatom Algae: Assimilation of Polycarbonic Acids with Diatoms—Is Endocytosis a Key Stage in Building of Siliceous Frustules?

Annenkov

Gordon²,

Zelinskiy

et al. 2020

Journal of Phycology

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Many organisms including unicellular (diatoms, radiolaria, and chrysophytes), higher plants (rice and horsetail) and animals (sponges) use silica as a main part of skeletons. The bioavailable form of silicon is silicic acid and the mechanism of silicic acid penetration into living cells is still an enigma. Macropinocytosis was assumed as a key stage of the silicon capture by diatoms but assimilation of monomeric silicic acid by this way requires enormous amounts of water to be passed through the cell. We hypothesized that silicon can be captured by diatoms via endocytosis in the form of partially condensed silicic acid (oligosilicates) whose formation on the diatom surface was supposed. Oligosilicates are negatively charged nanoparticles and similar to coils of poly(acrylic acid) (PAA). We have synthesized fluorescent tagged PAA as well as several neutral and positively charged polymers. Cultivation of the diatom Ulnaria ferefusiformis in the presence of these polymers showed that only PAA is able to penetrate into siliceous frustules. The presence of PAA in the frustules was confirmed with chromatography and PAA causes various aberrations of the valve morphology. Growth of U. ferefusiformis and two other diatoms in the presence of tri-and tetracarbonic fluorescent tagged acids points to the ability of diatoms to recognize substances that bear four acidic groups and to include them into siliceous frustules. Thus, partial condensation of silicic acid is a plausible first stage of silicon assimilation.

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Section: Methodsmentioning

confidence: 99%

The Probable Mechanism for Silicon Capture by Diatom Algae: Assimilation of Polycarbonic Acids with Diatoms—Is Endocytosis a Key Stage in Building of Siliceous Frustules?

Annenkov

Gordon²,

Zelinskiy

et al. 2020

Journal of Phycology

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“…Trimethyl aconitate 106 has been electrolyzed potentiostatically (−1.25 V) at a mercury cathode in DMF‐tetraethylammonium bromide to afford pentamethyl‐1‐(2‐methoxy‐2‐oxoethyl)‐1,2,3,4,5‐cyclopentane pentacarboxylate(Et 4 NBr) 107 (75 % yield and excellent stereoselectivity) and the side product 108 (Scheme ) …”

Section: Electrogenerated Based Michael Addition Reactionmentioning

confidence: 99%

“…The product structure, the substoichiometric current consumption and cyclovoltammetry demonstrate that product construction happens using a base that is electrogenerated from 106 . The base prompts a catalytic cycle of two successive Michael additions, where 106 serve as an acceptor and its conjugated base 108 as a donor (Scheme ) …”

Section: Electrogenerated Based Michael Addition Reactionmentioning

confidence: 99%

Electrochemically Induced Michael Addition Reaction: An Overview

Fotouhi

Heravi

Zadsirjan

et al. 2018

The Chemical Record

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Due to its high potential for the formation of carbon‐carbon bonds, Michael addition reaction is one of the closest reactions to the heart of synthetic organic chemists. Electrochemistry presents a very stimulating and divergent resource for selective oxidation and reduction in organic chemistry, generating activated species, for example radical anions or radical cations. In this review, we try to underscore usefulness of electrogenerated Michael addition reaction with the hope of encouraging synthetic organic chemists to contemplate it, as an efficient and green strategy when it is required in their designed multi‐step reaction pathways.

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“…[1] First systematic investigations demonstrate that the functional groups in 1 can be used for Michael additions, [2] Diels ± Alder cycloadditions, [3] Knoevenagel condensations, [4] and cyclodimerizations. [5] Here we report on domino reactions [6] of the donor(d) and acceptor(a) groups of 1 with imines.…”

Section: Dedicated To Professor Dieter Hoppe On the Occasion Of His 6mentioning

confidence: 99%

“…[3] We recently developed a fundamentally new class of enantioselective electrophilic fluorinating reagents (noted hereafter [N ± F] ) derived from cinchona alkaloids. [4] Independently, Shibata and co-workers reported a conceptually similar approach, [5] in which the chiral fluorinating agent was not isolated, but generated in situ. While these studies demonstrated the ability of enantioselective F transfer, further work must be undertaken to reach still higher enantioselectivities.…”

Section: Dedicated To Professor Dieter Hoppe On the Occasion Of His 6mentioning

confidence: 99%

Heterocycles through Domino Reactions with Trimethyl Aconitate, a Versatile Synthetic Building Block

Witthaut

Fröhlich

Schäfer

2001

Angew. Chem. Int. Ed.

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Cathodically initiated cyclodimerization of trimethyl aconitate

Cited by 13 publications

References 18 publications

The Probable Mechanism for Silicon Capture by Diatom Algae: Assimilation of Polycarbonic Acids with Diatoms—Is Endocytosis a Key Stage in Building of Siliceous Frustules?

The Probable Mechanism for Silicon Capture by Diatom Algae: Assimilation of Polycarbonic Acids with Diatoms—Is Endocytosis a Key Stage in Building of Siliceous Frustules?

Electrochemically Induced Michael Addition Reaction: An Overview

Heterocycles through Domino Reactions with Trimethyl Aconitate, a Versatile Synthetic Building Block

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