Stereoselective cyclopalladation of 2,3-camphorquinone 3-diphenylmethylimine

Gur’eva, Ya. A.; Zalevskaya, O. A.; Alekseev, I. N.; Фролова, Л. Л.; Слепухин, П. А.; Кучин, А. В.

doi:10.1007/s11172-014-0633-4

Cited by 8 publications

(5 citation statements)

References 5 publications

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“…Compared to preligands 5a,b, the DEPT spectra of dimers 7a,b contained one more CH 2 signal (at 24.6 ppm for 7a and at 25.8 ppm for 7b). For comparison, the 1 H NMR signals of two diastereotopic hydrogens of the PdCH 2 group in the camphor-derived complexes 3a,b appeared at 1.55 and 2.59 ppm (3a) and 1.89 and 2.41 ppm (3b); the 13 C{ 1 H} NMR signal of the carbon bonded to the metal in complexes 3a,b was observed at 30.2 and 29.9 ppm, respectively [9,10]. 13 C{ 1 H} NMR spectra of dimers 7a,b in CDCl 3 contained only one set of signals suggesting that these complexes exist in solution as one isomer.…”

Section: Resultsmentioning

confidence: 99%

“…provided singlets in the 13 C{ 1 H} NMR spectra at 35.1 and 27.0 ppm, respectively [9,10] X-ray structural analysis of complexes 8a,b…”

Section: Resultsmentioning

confidence: 99%

“…Other naturally occurring optically active compounds, which were used for preparation of palladacycles, include derivatives of (þ)-estrone [6] and D-camphor (1) [9e11]. For example, O-methyloxime [9] and N-benzylimine [10] of D-camphor (2a,b), which are readily synthesized in one step from ketone 1, undergo (sp 3 )CeH bond activation in the presence of Pd(OAc) 2 providing unique palladacycles 3a,b (Scheme 1). D-Camphor and many other bicyclic monoterpenoids possess rigid structures that may be an advantageous feature for chiral catalysts; therefore, CPCs based on compounds of this type are important research targets.…”

Section: Introductionmentioning

confidence: 99%

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Preparation and characterization of cyclopalladated complexes derived from l-(−)-fenchone

Dickmu

Smoliakova

2014

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

“…provided singlets in the 13 C{ 1 H} NMR spectra at 35.1 and 27.0 ppm, respectively [9,10] X-ray structural analysis of complexes 8a,b…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Preparation and characterization of cyclopalladated complexes derived from l-(−)-fenchone

Dickmu

Smoliakova

2014

Journal of Organometallic Chemistry

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“…The synthesis, physicochemical and spectral characteristics of the complexes 1-4, 6-12 have been reported previously [30][31][32][33][34][35][36]. The synthesis of the new complex 5 was carried out according to known procedures [31].…”

Section: Synthesis Of Complexesmentioning

confidence: 99%

Antimicrobial and Antifungal Activities of Terpene-Derived Palladium Complexes

et al. 2020

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In an era of multidrug-resistant bacterial infections overshadowed by a lack of innovation in the antimicrobial drug development pipeline, there has been a resurgence in multidisciplinary approaches aimed at tackling this global health problem. One such approach is to use metal complexes as a framework for new antimicrobials. Indeed, in this context, bismuth-, silver- and gold-derived compounds in particular have displayed demonstrable antimicrobial activity. In this work, we discuss the antimicrobial and antifungal activities of terpene-derived chiral palladium complexes against Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, Acinetobacter baumannii, Escherichia coli, Candida albicans, and Cryptococcus neoformans. It was established that all studied coordination compounds of palladium were highly active antifungal drugs. In contrast, the subset of palladacycles possessing a palladium–carbon bond were only active against the Gram-positive bacterium Staphylococcus aureus. All compounds were inactive against the Gram-negative bacteria tested.

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“…We previously reported the synthesis of chiral imines and amines from 2α-hydroxypinan-3-one [7]. The resulting nitrogen-containing derivatives were successfully used as ligands to obtain various palladium complexes [8,9]. …”

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confidence: 99%

Stereoselective synthesis of amino ketones of the pinane series

et al. 2015

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SHORT COMMUNICATIONSAt present, enantiomerically pure α-pinene and camphor derivatives are widely used in asymmetric syntheses as chiral auxiliaries [1], building blocks [2,3], and chiral ligands [4]. For example, terpene amino alcohols derived from 2α-hydroxypinan-3-one, were studied as enantioselective ligands in the ruthenium-catalyzed reduction of acetophenone [5], while palladium chelates with bornane diimines and diamines efficiently catalyzed asymmetric allylic substitution reactions [6]. According to published data, search for new enantiomerically pure ligands on the basis of commercially available initial compounds is a topical problem. We previously reported the synthesis of chiral imines and amines from 2α-hydroxypinan-3-one [7]. The resulting nitrogen-containing derivatives were successfully used as ligands to obtain various palladium complexes [8,9].

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Stereoselective cyclopalladation of 2,3-camphorquinone 3-diphenylmethylimine

Cited by 8 publications

References 5 publications

Preparation and characterization of cyclopalladated complexes derived from l-(−)-fenchone

Preparation and characterization of cyclopalladated complexes derived from l-(−)-fenchone

Antimicrobial and Antifungal Activities of Terpene-Derived Palladium Complexes

Stereoselective synthesis of amino ketones of the pinane series

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