Baker's‐Yeast‐Mediated Reduction of Sulfur‐Containing Compounds

Deasy, Rebecca E.; Maguire, Anita R.

doi:10.1002/ejoc.201301729

Cited by 12 publications

(11 citation statements)

References 147 publications

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“…However, the non-dynamic center results in two major diastereomeric products (Scheme 28). [63-64] Interestingly, in both cases here, two essentially enantiopure diastereomers are obtained, yet the reported diastereomeric ratio is not 1:1, nor is the overall yield quantitative, as it should be, in the ideal case of a ‘silent’ pre-existing stereocenter. It thus appears likely in these cases, that the pre-existing stereocenter is not ‘silent,’ but rather that the ADH (or ADHs) present act at a differential rate upon the two enantiomeric ketone substrates, sensing this center in this way.…”

Section: Future Challengesmentioning

confidence: 70%

“…[63] While β-keto thioethers appear to be processed via simple (non-dynamic) kinetic resolution, β-keto sulfones under efficient DYRKR under these conditions. However, as the ring size increases to 7 for cyclic β-keto sulfones, a drastic decrease in yield is observed (8%, n=3).…”

Section: Other β-Keto-systemsmentioning

confidence: 99%

“…The DYRKR still proceeds efficiently providing the β-hydroxy cyclic sulfone in an overall syn manner with high enantioselectivity. [63] …”

Section: Other β-Keto-systemsmentioning

confidence: 99%

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Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis

Applegate

Berkowitz

2015

Adv Synth Catal

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Over the past two decades, the domains of both frontline synthetic organic chemistry and process chemistry and have seen an increase in crosstalk between asymmetric organic/organometallic approaches and enzymatic approaches to stereocontrolled synthesis. This review highlights the particularly auspicious role for dehydrogenase enzymes in this endeavor, with a focus on dynamic reductive kinetic resolutions (DYRKR) to “deracemize” building blocks, often setting two stereocenters in so doing. The scope and limitations of such dehydrogenase-mediated processes are overviewed, as are future possibilities for the evolution of enzymatic DYRKR.

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Section: Future Challengesmentioning

confidence: 70%

Section: Other β-Keto-systemsmentioning

confidence: 99%

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Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis

Applegate

Berkowitz

2015

Adv Synth Catal

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“…Among asymmetric biotransformations, the stereoselective reduction of carbonyl compounds catalyzed by alcohol dehydrogenases (ADHs, E.C.1.1.1.1, also known as ketoreductases or carbonyl reductases) provides an elegant manner to produce optically active alcohols by using purified or whole‐cell enzyme forms . Interestingly, the versatility of ADHs has been widely demonstrated for the stereoselective reduction of a broad range of prochiral carbonyl compounds, including β‐nitroketones, β‐keto amides or ketones containing halogens, sulfur, boron and others functionalities …”

Section: Introductionmentioning

confidence: 99%

Stereoselective Bioreduction of Telluro‐Acetophenones to Optically Active Hydroxy Tellurides

2020

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Organotellurium compounds exhibit a broad range of useful applications in organic synthesis, materials science and medicinal chemistry fields. Despite their increasing applicability, the synthesis of enantiomerically pure organotellurium compounds remains nowadays scarcely reported in the literature. Herein, the chemical synthesis and biocatalyzed reductions of a set of telluro‐acetophenones using both (R) and (S)‐selective alcohol dehydrogenases (ADHs) is described for the first time, obtaining enantiomerically enriched hydroxy tellurides with excellent selectivities under very mild reaction conditions. On the one hand, enantiopure para‐substituted (S)‐hydroxy tellurides were obtained using the Ras‐ADH (77–95 % conversion) and ADH‐A (52–75 %), the ADH‐A leading to the enantiopure (S)‐hydroxy tellurides substituted at the meta‐position (69–75 %). On the other hand, the evo‐1.1.200 displayed high selectivity towards the preparation of optically alcohols with substitutions at the para‐position of the aromatic ring (60–68 % conversion and 92–97 % ee), while the Lb‐ADH led to the best results when reducing bulky ketones at the meta‐position (79–82% conversion and 88–99 % ee).

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“…This is largely due to the ready availability, ease of experimental procedures and versatility of this microorganism [1][2][3][4][5]. Both the efficiency and stereoselectivity in baker's yeast mediated reduction of ketones is strongly influenced by both the presence and the position of sulfur substituents or indeed by the use of sulfur containing additives [6,7].…”

Section: Introductionmentioning

confidence: 99%