Asymmetric Synthesis of (<i>S</i>)‐2‐Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis

Lange, Ben de; Hyett, David J.; Maas, Peter J. D.; Mink, Daniel; Assema, Friso B. J. van; Sereinig, N.; Vries, André H.M. de; Vries, Johannes G. de

doi:10.1002/cctc.201000435

Cited by 108 publications

(76 citation statements)

References 23 publications

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“…Regarding the use of PAL enzymes for the synthesis of chiral intermediates, probably the most interesting example is the synthesis of the chiral indoline carboxylic acid 46 , Scheme . Fischer indole synthesis followed by classical or enzymatic resolution is the common way to synthesize this type of carbon skeleton 46 , but yields never exceeded 50 %.…”

Section: Functional Group Analysismentioning

confidence: 99%

“…An alternative is the use of a PAL enzyme to produce the chiral amine 52 , prior to the cyclization step, in order to construct the chiral C−N bond between ammonia and the cinnamic acid derivative 50 . The product obtained by this reaction is a phenylalanine derivative 52 , which is ready for cyclization into the desired product (Scheme ) …”

Section: Functional Group Analysismentioning

confidence: 99%

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A Retrosynthesis Approach for Biocatalysis in Organic Synthesis

Souza

Miranda

Bornscheuer

2017

Chemistry A European J

186

104

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For the planningo fa no rganic synthesis route, the disconnection approach guided by retrosynthetic analysis of possible intermediates and the chemical reactions involved, backt or eady available starting materials, is well established. In contrast, such concepts just get developed for biocatalytic routes. In this Review we highlightf unctional group interconversions catalyzed by enzymes. The article is organized rather by chemical bonds formed-exemplified for CÀN, CÀO-and CÀC-bonds-and not by enzyme classes, covering ab road range of reactions to incorporate the desired functionality in the target molecule. Furthermore, the successful use of biocatalysts, also in combination with chemicals teps, is exemplified for the synthesis of various drugs and advanced pharmaceutical intermediates such as Crispine A, Sitagliptina nd Atorvastatin. This Reviewa lso provides some basic guidelines to choose the most appropriate enzyme for at argeted reaction keepingi nm ind aspects like commercial availability,c ofactor-requirement, solventt olerance, use of isolated enzymes or whole cell recombinant microorganisms aiming to assist organic chemists in the use of enzymesf or synthetic applications.

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Section: Functional Group Analysismentioning

confidence: 99%

Section: Functional Group Analysismentioning

confidence: 99%

A Retrosynthesis Approach for Biocatalysis in Organic Synthesis

Souza

Miranda

Bornscheuer

2017

Chemistry A European J

186

104

View full text Add to dashboard Cite

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“…Verbindung 3 ist ein wichtiges Zwischenprodukt bei der Herstellung der ACE‐Inhibitoren Indolapril und Perindopril für die Behandlung von Bluthochdruck. Dieses Verfahren wurde von DSM Pharma Chemicals entwickelt und nutzt Aminosäuren 2 (hergestellt aus Säuren 1 über eine enantioselektive enzymatische Reaktion) als Startmaterial. Die Cu‐katalysierte intramolekulare Arylaminierung von 2 verläuft problemlos bei ca.…”

Section: Cu‐katalysierte Kreuzkupplungen Von Arylhalogeniden Mit Nuclunclassified

Ausgewählte Kupfer‐katalysierte Reaktionen für die Bildung von C‐N‐, C‐O‐, C‐S‐ und C‐C‐Bindungen

et al. 2017

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Die metallkatalysierte Kreuzkupplung ist eine der wichtigsten Umwandlungen der organischen Synthese. Aufgrund der geringen Toxizität und des günstigen Preises von Kupfer hat die Kupferkatalyse viel Interesse geweckt. Die traditionelle Ullmann‐Kupplung hat jedoch eine geringe Substratbreite und erfordert harsche Reaktionsbedingungen. In den vergangenen zwei Jahrzehnten wurden zweizähnige Liganden, z. B. Aminosäuren, Diamine, 1,3‐Diketone und Oxalsäurediamide, eingeführt, die Cu‐katalysierte Kupplungen von Arylhalogeniden und Nucleophilen sowohl bei niedrigen Temperaturen als auch in katalytischer Weise ermöglichen. Dadurch ist die Cu‐vermittelte Kreuzkupplung zu einer attraktiven Reaktion für die akademische Forschung und die Industrie geworden. Dieser Aufsatz fasst Fortschritte bei Kupplungen von (Hetero)Arylhalogeniden mit verschiedenen Nucleophilen zusammen und stellt Entwicklungen bei Cu‐katalysierten Kupplungen mit Arylboronaten und Cu‐vermittelten Trifluormethylierungen von aromatischen Elektrophilen vor.

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“…This procedure is currently used for ton-scale production by DSM Pharma Chemicals. [17] The compound 29 is a new drug candidate developed by UCB Pharma based on the structure of Levetiracetam, a clinically used drug for treatment of epilepsy. After screening several possible routes for producing this compound in large scale, they found that a coupling protocol is scalable.…”

Section: Applications In Large-scale Productionmentioning

confidence: 99%