Asymmetric transfer hydrogenation of aromatic ketones by Rh(I)/bimorpholine complexes

Kriis, Kadri; Kanger, Tõnis; Lopp, Margus

doi:10.1016/j.tetasy.2004.07.017

Cited by 19 publications

(6 citation statements)

References 23 publications

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“…[1,14] An alternative approach to synthesize enantiomerically enriched diarylmethanols is the reduction of diaryl ketones, [1] which can be achieved chemically and biocatalytically. The asymmetric chemical reductions of diaryl ketones involve chiral borane reduction, [15][16][17] transition metal-catalyzed hydrogenation, [18][19][20] hydrogen transfer reduction [21] , and hydrosilylation. [22][23][24] Although these chemical methods have provided a useful access to diarylmethanol with high enantiomeric purity in some cases, their common drawback is the limited substrate range.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Reduction of Diaryl Ketones Catalyzed by a Carbonyl Reductase from Sporobolomyces salmonicolor and its Mutant Enzymes

Zhu

Ling³

et al. 2009

Adv Synth Catal

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Abstract:The carbonyl reductase from red yeast Sporobolomyces salmonicolor AKU4429 (SSCR) and its mutant enzymes effectively catalyzed the enantioselective reduction of diaryl ketones to give the corresponding chiral alcohols. Both conversion and enantioselectivity were dependent on the co-solvent in the reaction medium. Diaryl ketones with a para-substituent on one of the phenyl groups were reduced with high enantioselectivity (up to 99% ee), which is difficult to achieve using chemical methods such as chiral borane reduction, asymmetric hydrogenation or hydrosilylation. Mutation of SSCR at Q245 resulted in a higher amount of (S)-enantiomer in the products, and in the case of mutant Q245P with para-substituted diaryl ketones as substrate, this effect was so remarkable that the reduction enantiopreference was switched from (R) to (S). The present study provides valuable information about the catalytic properties of the carbonyl reductase SSCR toward the reduction of diaryl ketones, serving as basis for further engineering of this enzyme to develop efficient biocatalysts for highly enantiospecific reduction of diaryl ketones without high electronic dissymmetry or an ortho-substituent on one of the aryl groups.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Reduction of Diaryl Ketones Catalyzed by a Carbonyl Reductase from Sporobolomyces salmonicolor and its Mutant Enzymes

Zhu

Ling³

et al. 2009

Adv Synth Catal

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“…The preliminary results demonstrating high efficiency and high stereoselectivity of the catalysts in organocatalytic Michael additions and in intramolecular aldol condensations have been recently published. Furthermore, bimorpholine 2 (or its derivatives) is also useful as a chiral ligand in the transition-metal-catalyzed asymmetric hydrogenation …”

Section: Introductionmentioning

confidence: 99%

Bimorpholine-Mediated Enantioselective Intramolecular and Intermolecular Aldol Condensation

et al. 2007

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Monosalts of N-substituted bimorpholine derivatives are efficient organocatalysts in intramolecular and intermolecular aldol reactions. The properties of the catalysts can be tuned either by the selection of an appropriate acid for the salt formation or by the change of a substituent at the nitrogen atom. In aldol condensation, i-Pr-substituted bimorpholine is the most stereoselective catalyst affording products in high yield with enantioselectivities up to 95% ee.

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“…112 The area of asymmetric transfer hydrogenation continues to attract keen interest. New ligand systems have been developed for ruthenium, [113][114][115] iridium [116][117][118][119] and rhodium catalysis. 120 Transfer hydrogenation of a-chloro ketones has been examined 121 allowing an ensuing entry to chiral epoxides with high e.e.…”

Section: Reduction Of Carbonyl Compoundsmentioning

confidence: 99%

2 Synthetic methods : Part (ii) Oxidation and reduction methods

Armstrong

Carbery

2005

Annu. Rep. Prog. Chem., Sect. B

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Asymmetric transfer hydrogenation of aromatic ketones by Rh(I)/bimorpholine complexes

Cited by 19 publications

References 23 publications

Enantioselective Reduction of Diaryl Ketones Catalyzed by a Carbonyl Reductase from Sporobolomyces salmonicolor and its Mutant Enzymes

Enantioselective Reduction of Diaryl Ketones Catalyzed by a Carbonyl Reductase from Sporobolomyces salmonicolor and its Mutant Enzymes

Bimorpholine-Mediated Enantioselective Intramolecular and Intermolecular Aldol Condensation

2 Synthetic methods : Part (ii) Oxidation and reduction methods

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