Stereospecific co-crystallization of reactant and palladium complex in the resolution of stilbendiamine using N*-chiral ortho-palladated matrix

Dunina, V. V.; Кузьмина, Л. Г.; Parfyonov, A. G.; Grishin, Yuri K.

doi:10.1016/s0957-4166(98)00176-1

Cited by 18 publications

(2 citation statements)

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“…109 Other examples of resolutions involving cyclopalladated compounds are illustrated in Chart 17 including the chiral cyclic phosphine 100. 110 Chelating ligands such as the important pharmaceutical feedstock 101 111 and amino sulfoxides or diamines such as 102 112 and 103 113 have all been successfully resolved using the techniques described earlier. A curious resolution involving an achiral cyclopalladated complex is also worthy of inclusion in this discussion, since the diastereomers of a stibane were only separable once bound to a palladium as in the complex 104.…”

Section: Chiral Cyclopalladated Compounds As Resolution Agentsmentioning

confidence: 99%

The Potential of Palladacycles: More Than Just Precatalysts

2005

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Section: Chiral Cyclopalladated Compounds As Resolution Agentsmentioning

confidence: 99%

The Potential of Palladacycles: More Than Just Precatalysts

2005

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“…Fig 48. Binary phase diagrams of enantiomeric mixtures: (a) conglomerate, (b) formation of a separate racemic phase ("racemate").…”

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confidence: 99%

Optical resolution methods

et al. 2006

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Despite the large number of elaborate enantioselective syntheses for the preparation of a single enantiomer to achieve industrial and scientific goals, the separation and purification of enantiomers (components of racemic compounds) is also necessary. Hence, we present the most often used thought-provoking modern methods based on momentous recognitions (e.g. spontaneous resolution, induced crystallization, resolution by formation of diastereomers, resolution by formation of non-covalent diastereomers, resolution by diastereomeric salt formation, resolution by diastereomeric complex formation, "half equivalent" methods of resolution, separation by crystallization, separation by distillation, separation by supercritical fluid extraction, resolution with mixtures of resolving agents, resolution with a derivative of the target compound, enantioselective chromatography, resolution by formation of covalent diastereomers, resolution by substrate selective reaction, kinetic resolution without enzymes, kinetic resolution by enzyme catalysis, hydrolytic and redox enzymes, kinetic and thermodynamic control, resolutions combined with 2nd order asymmetric transformations, enrichment of partially resolved mixtures, role of the solvent and methods of optimization in the separation of diastereoisomers, non-linear effects and selected examples of resolution on an industrial scale).

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Steric Promotion of Aromatic C–H Bond Activation in Primary Benzylamines

Dunina¹,

Кузьмина

Kazakova

et al. 1999

Eur. J. Inorg. Chem.

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ortho‐Palladation of a sterically crowded primary benzylamine, α‐phenylneopentylamine, was accomplished in a moderate yield of 50% in the reaction with the weakest of palladation agents (Li2PdCl4) under very mild conditions, due to a steric promotion of an aromatic C–H bond activation. The structure of dimer 1a thus formed and the palladacycle conformation were established on the basis of 1H‐NMR spectroscopy of its mononuclear derivatives with [D5]pyridine (3a) and triphenylphosphane (4a), and an X‐ray investi‐gation of the latter.

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Stereospecific co-crystallization of reactant and palladium complex in the resolution of stilbendiamine using N*-chiral ortho-palladated matrix

Cited by 18 publications

References 6 publications

The Potential of Palladacycles: More Than Just Precatalysts

The Potential of Palladacycles: More Than Just Precatalysts

Optical resolution methods

Steric Promotion of Aromatic C–H Bond Activation in Primary Benzylamines

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