Guanidine Organocatalysis

Selig, Philipp

doi:10.1055/s-0032-1318154

Cited by 141 publications

(63 citation statements)

References 44 publications

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“…1-4 The ability of this highly polar and basic functional group in establishing strong ionic/hydrogen bonding 5 and cation-π stacking 6,7 interactions with various functional groups has made it particularly useful in the design of small-molecule drugs, metal ligands, and organocatalysts. Additionally, many naturally occurring polycyclic guanidine derivatives possess useful and potent biological properties.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.

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Section: Introductionmentioning

confidence: 99%

Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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“…Recently, a number of excellent reviews on guanidine organocatalysis exist because of their high charge dispersion and excellent thermal and chemical stabilities owing to their special structures [5][6][7][8][9][10][11]. Despite this wealth of functionality present in guanidine, the synthesis of guanidinium-based Brønsted acid has not been reported previously.…”

Section: Introductionmentioning

confidence: 99%

Guanidinium-based sulfonic acid as a new Brønsted acid organocatalyst in organic synthesis in water

et al. 2015

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Guanidinium-based sulfonic acid as a new Brønsted acid organocatalyst has been synthesized, characterized, and applied for the synthesis of 3,4-dihydroquinoxalin-2-amine, 1,6-dihydropyrazine-2,3-dicarbonitrile, triazolo[1,2-a]indazole-trione, and spiro triazolo[1,2-a]indazole-tetraone derivatives in an aqueous medium. The catalytic system, reported here, possesses the advantages of both homogeneous and heterogeneous catalysts and can be repetitively used in water. Graphical Abstract& Ahmad Shaabani a-

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“…3 The guanidinium moiety has been widely explored as strong and selective binder for anionic guests and was used in the design of anion receptors in supramolecular chemistry, 4 anion transporters across lipid bilayers and membranes, 5 colorimetric probes, and sensors. 6 Guanidine organocatalysis 7 and biological activities of guanidine compounds 8 have been reviewed recently. Unsubstituted guanidine itself is one of compounds important for prebiotic and astro-chemistry as well.…”

Section: Introductionmentioning

confidence: 99%

Guanidine and guanidinium cation in the excited state—theoretical investigation

Antol

Glasovac

Crespo‐Otero

et al. 2014

The Journal of Chemical Physics

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Diverse ab initio and density-functional-theory methods were used to investigate geometries, energies, and electronic absorption spectra of guanidine and its protonated form, as well as their photo-deactivation processes. It was shown that the guanidine is a weakly absorbing species with the excitation spectrum consisting mostly of transitions to the Rydberg excited states and one valence n-π4 state. The lowest energy band has a maximum at ca. 6.9 eV (∼180 nm). The protonation of guanidine affects its excitation spectrum substantially. A major shift of the Rydberg states to higher energies is clearly visible and strongly absorbing transitions from the ground state to the π3-π4 and π2-π4 states appears at 7.8 eV (∼160 nm). Three low-lying conical intersections (two for guanidine and one for protonated guanidine) between the ground state and the first excited singlet state were located. They are accessible from the Franck-Condon region through amino N-H stretching and out-of-plane deformations in guanidine and protonated guanidine, respectively. The relaxation of the π3-3s Rydberg state via amino N-H bond stretching was hindered by a barrier. The nondissociated conical intersection in protonated guanidine mediates the radiationless deactivation of the compound after excitation into the π3-π4 state. This fact is detrimental for the photostability of guanidine, since its conjugate acid is stable in aqueous solution over a wide pH range and in protein environment, where guanidinium moiety in arginine is expected to be in a protonated form.

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Guanidine Organocatalysis

Cited by 141 publications

References 44 publications

Syntheses of cyclic guanidine-containing natural products

Syntheses of cyclic guanidine-containing natural products

Guanidinium-based sulfonic acid as a new Brønsted acid organocatalyst in organic synthesis in water

Guanidine and guanidinium cation in the excited state—theoretical investigation

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