Enantioselective reduction of prochiral ketones by chromium(II) complexes with amino acid ligands as the source of chirality

Patonay, Tamás; Hajdu, Csongor; Jekő, József; Lévai, Albert; Micskei, Károly; Zucchi, Claudia

doi:10.1016/s0040-4039(98)02611-2

Cited by 17 publications

(4 citation statements)

References 7 publications

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“…A new application of chirally modified chromium(II) was recently discovered by Micskei et al, who could reduce aryl ketones like acetophenone (184) to the corresponding alcohol with up to 55% ee. 326…”

Section: Ligand Based Methodsmentioning

confidence: 99%

Recent Advances in Chromium(II)- and Chromium(III)-Mediated Organic Synthesis

Wessjohann¹,

Scheid²

1999

Synthesis

215

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Synthetic transformations utilizing chromium(II) or chromium(III) reagents, mainly CÐC-coupling reactions, are discussed. Chromium reagents find increasing application in complex total syntheses where other organometallics are difficult to apply. They are easy to prepare and exhibit extraordinary chemoselectivity and high diastereoselectivity. In this article emphasis is laid on recent results in synthetic procedures, on little known general aspects of (organo)chromium chemistry, and on areas not reviewed before. The most important recent advances include reactions catalytic in chromium ions, anti -selective Reformatsky-type aldol reactions with excellent asymmetric induction, domino radical/carbanion reactions, asymmetric chromium(III) catalyzed epoxide openings and homogeneous alkene polymerization catalysts. Some progress is also made in ligand controlled enantioselective reactions with Cr(II) reagents, but satisfying solutions remain a major challenge in the field.

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Section: Ligand Based Methodsmentioning

confidence: 99%

Recent Advances in Chromium(II)- and Chromium(III)-Mediated Organic Synthesis

Wessjohann¹,

Scheid²

1999

Synthesis

215

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“…10 Amplification of one molecule enantiomeric excess in consecutive one-pot Soai reaction cycles to macroscopically significant ees As the starting point the experience of the Debrecen group with the use of Cr(II) complexes in reduction of organic functional groups [127][128][129] was utilized, with the modification, that for N,O-donor ligands we chose pure enantiomers of amino acids. This reducing system was first tested in the reduction of various ketonic substrates [130][131][132], then with ketoximes [133]. In both cases medium to high enantiomeric excesses were found in the products.…”

Section: Toward Designed Soai-type Systems?mentioning

confidence: 99%

Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis

et al. 2015

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Absolute asymmetric synthesis (AAS) is the preparation of pure (or excess of one) enantiomer of a chiral compound from achiral precursor(s) by a chemical reaction, without enantiopure chiral additive and/or without applied asymmetric physical field. Only one well-characterized example of AAS is known today: the Soai-autocatalysis. In an attempt at clarification of the mechanism of this particular reaction we have undertaken empirical and stochastic analysis of several parallel AAS experiments. Our results show that the initial steps of the reaction might be controlled by simple normal distribution ("coin tossing") formalism. Advanced stages of the reaction, however, appear to be of a more complicated nature. Symmetric beta distribution formalism could not be brought into correspondence with the experimental observations. A bimodal beta distribution algorithm provided suitable agreement with the experimental data. The parameters of this bimodal beta function were determined by a Pólya-urn experiment (simulated by computer). Interestingly, parameters of the resulting bimodal beta function give a golden section ratio. These results show, that in this highly interesting autocatalysis two or even perhaps three catalytic cycles are cooperating. An attempt at constructing a "designed" Soai-type reaction system has also been made.

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“…Simplified models, for bioimitating systems, with biology-related substrates are extensively studied in our Laboratories, in collaboration with the University of Debrecen (Gyarmati et al 1999;Patonay et al 1999;Micskei et al 2003Micskei et al , 2005b. The main message of these studies is, that biology-related ligands (amino acids) can be successfully used as sources of chirality on transition metal templates (Cr(II)), even for the preparation of products of the opposite configuration with respect to the chiral inductor.…”

Section: Living Organisms Under Extraterrestrial Conditionsmentioning

confidence: 99%

Astrobiology and Biological Chirality

Caglioti

Holczknecht

Fujii

et al. 2006

Orig Life Evol Biosph

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The emerging discipline of astrobiology could gain valuable support from research dealing with the problems of biological chirality. The most profitable fields of common interest are: (a) living organisms under extraterrestrial conditions, (b) extraterrestrial signatures of life and (c) origin(s) of biological chirality. These areas of complementary and overlapping fields are analysed on the basis of selected references.

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Enantioselective reduction of prochiral ketones by chromium(II) complexes with amino acid ligands as the source of chirality

Cited by 17 publications

References 7 publications

Recent Advances in Chromium(II)- and Chromium(III)-Mediated Organic Synthesis

Recent Advances in Chromium(II)- and Chromium(III)-Mediated Organic Synthesis

Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis

Astrobiology and Biological Chirality

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