Industrial Methods for the Production of Optically Active Intermediates

Breuer, Michael; Ditrich, K.; Habicher, Tilo; Hauer, Bernhard; Keßeler, Maria; Stuermer, Rainer; Zelinski, Thomas

doi:10.1002/chin.200420289

Cited by 62 publications

(76 citation statements)

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“…For these applications high purities and large quantities are required. Initially the chemical industry applied established chemical synthesis routes for their production, but is turning more and more to biocatalytic processes (Balkenhohl et al, 1997;Breuer et al, 2004;Schmid et al, 2002;Sheldon, 2007;Woodley, 2008). Nowadays, biocatalysis can be considered as standard technology for the production of hydrophobic fine chemicals and is applied by companies such as BASF, DSM, Lonza, Dow Chemical, and DuPont (Schmid et al, 2001;Sheldon, 2005;Straathof et al, 2002).…”

Section: Table 4-1mentioning

confidence: 99%

Model-based experimental analysis of enzyme kinetics in aqueous–organic biphasic systems

Zavrel

Schmidt

Michalik

et al. 2007

Journal of Biotechnology

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Section: Table 4-1mentioning

confidence: 99%

Model-based experimental analysis of enzyme kinetics in aqueous–organic biphasic systems

Zavrel

Schmidt

Michalik

et al. 2007

Journal of Biotechnology

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“…Enantiomerically pure amines are key intermediates in a number of pharmaceutical compounds that possess a wide range of biological activities 48 . In comparison with alcohols, the resolution of amines is more challenging as amines are more reactive than alcohols and tend to dissociate MOF structures.…”

mentioning

confidence: 99%

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

et al. 2014

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The separation of racemic molecules is of substantial significance not only for basic science but also for technical applications, such as fine chemicals and drug development. Here we report two isostructural chiral metal-organic frameworks decorated with chiral dihydroxy or -methoxy auxiliares from enantiopure tetracarboxylate-bridging ligands of 1,1 0 -biphenol and a manganese carboxylate chain. The framework bearing dihydroxy groups functions as a solid-state host capable of adsorbing and separating mixtures of a range of chiral aromatic and aliphatic amines, with high enantioselectivity. The host material can be readily recycled and reused without any apparent loss of performance. The utility of the present adsorption separation is demonstrated in the large-scale resolution of racemic 1-phenylethylamine. Control experiments and molecular simulations suggest that the chiral recognition and separation are attributed to the different orientations and specific binding energies of the enantiomers in the microenvironment of the framework.

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“…68,81 The existence of a mirror image relationship between enantiomers has an important consequence. Racemic solids may crystallize from solution in four different forms, namely (Figure 1.40):…”

Section: Spontaneous Resolution and Preferential Crystallizationmentioning

confidence: 99%