Chiral Brønsted Acid Catalyzed Kinetic Resolutions

Petersen, Kimberly S.

doi:10.1002/ajoc.201600021

Cited by 47 publications

(5 citation statements)

References 58 publications

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“…Moreover, some of these metabolites have been widely used as substrates in biotransformations catalyzed by specific enzymes for the preparation of complex natural and non‐natural compounds (Busto, ; Schmidt et al, ). Phosphate di‐ and triesters are also widely used in synthetic chemistry, for example, as Brønsted acid catalysts (Petersen, ; Terada, ) and as leaving groups in transition‐metal‐catalyzed coupling reactions (Murahashi et al, ; Trost and Czabaniuk, ; Yanagisawa et al, ). Finally, the use of phosphate esters as prodrugs is a common strategy to enhance solubility and bioavailability of drug candidates (Rautio et al, ; Schultz, ; Zawilska et al, ).…”

Section: Introductionmentioning

confidence: 99%

Investigation of acid phosphatase variants for the synthesis of phosphate monoesters

Tasnádi

Zechner

Hall

et al. 2017

Biotech & Bioengineering

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The major drawback of using phosphatases for transphosphorylation reactions lies in product depletion caused by the natural hydrolytic activity of the enzymes. Variants of PhoC-Mm from Morganella morganii and NSAP-Eb from Escherichia blattae were studied for their ability to maintain a high product level in the transphosphorylation of various primary alcohols. A single amino acid exchange delivered phosphatase variant PhoC-Mm G92D, which was able to catalyze the phosphorylation of primary alcohols without any major hydrolysis of the formed phosphate esters. The mutation mostly improved the affinity of the enzyme for alcohols, while rate constants of transphosphorylation and hydrolysis were decreased, overall resulting in a superior catalytic efficiency in transphosphorylation compared to hydrolysis. The presence of residual substrate alcohol at a given concentration was crucial to suppress phosphate ester hydrolysis. The present work extends the synthetic applicability of phosphatase variants beyond the previously reported nucleosides and allows preparative-scale production of various primary phosphate esters (yields up to 42%) with high enzyme productivity (TONs up to ∼66,000). Biotechnol. Bioeng. 2017;114: 2187-2195. © 2017 Wiley Periodicals, Inc.

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Section: Introductionmentioning

confidence: 99%

Investigation of acid phosphatase variants for the synthesis of phosphate monoesters

Tasnádi

Zechner

Hall

et al. 2017

Biotech & Bioengineering

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“…In 2020, we successfully achieved a magnesium-catalyzed 32 vinylogous-Michael type intramolecular KR reaction, which can be used for the rapid synthesis of complex chiral parallel [6,6,5]-tricyclic skeletons. 33 The reaction showed wide applicability to different alkyl-and aryl-substituted substrates and afforded high enantioselectivities of tricyclic products (Scheme 22).…”

Section: Michael Reaction-based Intramolecular Krmentioning

confidence: 99%

“…For example, Vedejs and Pellissier independently reviewed catalytic non-enzymatic kinetic resolution recently. 4 In 2016, a chiral Brønsted acid-catalyzed kinetic resolution was reviewed by Petersen and co-workers 5 and organocatalytic kinetic resolution was reviewed by Chen and co-workers. 6 Namboothiri et al presented a review of kinetic and dynamic kinetic resolution by dual catalysis in 2022.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in intramolecular kinetic resolution reactions

Peng

Yang

et al. 2023

Org. Chem. Front.

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“…As one of the most powerful organocatalysts, CPAs have also been widely utilized in the kinetic resolution and enantioselective desymmetrization reactions. In 2016, Petersen summarized the development of (dynamic) kinetic resolution enabled by chiral phosphoric acid catalysis [3h] . While the research of CPA‐catalyzed enantioselective desymmetrizations had not been specially reviewed, Dixon and co‐workers made a comprehensive review on organocatalyzed enantioselective desymmetrization in 2016, [6a] which included the examples catalyzed by CPA catalysts.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in (Dynamic) Kinetic Resolution and Desymmetrization Catalyzed by Chiral Phosphoric Acids

Liu

Yang

2021

Asian J Org Chem

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Kinetic resolution, dynamic kinetic resolution and desymmetrization are practical methods to produce enantioenriched products from relatively simple racemic or achiral starting materials, which are also sometimes difficult to be accessed by other asymmetric methods. Chiral phosphoric acids, which have been recognized as one of the most powerful chiral organocatalysts to date, have also been extensively applied in the above-mentioned research fields.In this minireview, we summarized the tremendous development of kinetic resolution, dynamic kinetic resolution and desymmetrization reactions enabled by chiral phosphoric acids since the year of 2016, which were not included in the two previous outstanding reviews by Petersen et al and Dixon et al. A number of examples involving the use of CPA as cooperative catalyst are also included in this review.Scheme 1. KR of β-amino alcohols via CPA-catalyzed p-methoxybenzylations.

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Chiral Brønsted Acid Catalyzed Kinetic Resolutions

Cited by 47 publications

References 58 publications

Investigation of acid phosphatase variants for the synthesis of phosphate monoesters

Investigation of acid phosphatase variants for the synthesis of phosphate monoesters

Recent advances in intramolecular kinetic resolution reactions

Recent Advances in (Dynamic) Kinetic Resolution and Desymmetrization Catalyzed by Chiral Phosphoric Acids

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