Diastereoselective Synthesis of an Industrially Relevant 4-Aminopentanoic Acid by Asymmetric Catalytic Hydrogenation in a Biphasic System Using Aqueous Sodium Hydroxide as Substrate Phase.
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| Title: | Diastereoselective Synthesis of an Industrially Relevant 4-Aminopentanoic Acid by Asymmetric Catalytic Hydrogenation in a Biphasic System Using Aqueous Sodium Hydroxide as Substrate Phase. |
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| Authors: | Piscopo, Calogero G.1, Gallou, Fabrice2, Leitner, Walter1 leitner@itmc.rwth-aachen.de, Franciò, Giancarlo1 francio@itmc.rwth-aachen.de |
| Source: | Synthesis. 2017, Vol. 49 Issue 2, p353-357. 5p. |
| Subjects: | Asymmetric synthesis, Hydrogenation, Sodium hydroxide, Solution (Chemistry), Homogeneous catalysis, Chemical derivatives |
| Abstract: | A 'basic solution' for multiphase catalysis: The diastereoselective synthesis of a pharmaceutically relevant 4-aminopentanoic acid derivative has been studied using a chiral homogeneous catalyst in tailored biphasic reaction media. Different polar solvents were investigated as the stationary phase for the well-established Ru-Mandyphos catalyst in combination with aqueous NaOH as the substrate and product phase. Facile product isolation and effective recycling of the catalyst phase were demonstrated at gram-scale. In particular, up to 3200 turnovers have been achieved in seven repetitive batches with a diastereoselectivity of 87-96% using [EMIM][NTf2]/NaOHaq as the biphasic system. [ABSTRACT FROM AUTHOR] |
| Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 120374065 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Diastereoselective Synthesis of an Industrially Relevant 4-Aminopentanoic Acid by Asymmetric Catalytic Hydrogenation in a Biphasic System Using Aqueous Sodium Hydroxide as Substrate Phase. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Piscopo%2C+Calogero+G%2E%22">Piscopo, Calogero G.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Gallou%2C+Fabrice%22">Gallou, Fabrice</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Leitner%2C+Walter%22">Leitner, Walter</searchLink><relatesTo>1</relatesTo><i> leitner@itmc.rwth-aachen.de</i><br /><searchLink fieldCode="AR" term="%22Franciò%2C+Giancarlo%22">Franciò, Giancarlo</searchLink><relatesTo>1</relatesTo><i> francio@itmc.rwth-aachen.de</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Synthesis%22">Synthesis</searchLink>. 2017, Vol. 49 Issue 2, p353-357. 5p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Asymmetric+synthesis%22">Asymmetric synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrogenation%22">Hydrogenation</searchLink><br /><searchLink fieldCode="DE" term="%22Sodium+hydroxide%22">Sodium hydroxide</searchLink><br /><searchLink fieldCode="DE" term="%22Solution+%28Chemistry%29%22">Solution (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Homogeneous+catalysis%22">Homogeneous catalysis</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+derivatives%22">Chemical derivatives</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: A 'basic solution' for multiphase catalysis: The diastereoselective synthesis of a pharmaceutically relevant 4-aminopentanoic acid derivative has been studied using a chiral homogeneous catalyst in tailored biphasic reaction media. Different polar solvents were investigated as the stationary phase for the well-established Ru-Mandyphos catalyst in combination with aqueous NaOH as the substrate and product phase. Facile product isolation and effective recycling of the catalyst phase were demonstrated at gram-scale. In particular, up to 3200 turnovers have been achieved in seven repetitive batches with a diastereoselectivity of 87-96% using [EMIM][NTf2]/NaOHaq as the biphasic system. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1055/s-0036-1588910 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 5 StartPage: 353 Subjects: – SubjectFull: Asymmetric synthesis Type: general – SubjectFull: Hydrogenation Type: general – SubjectFull: Sodium hydroxide Type: general – SubjectFull: Solution (Chemistry) Type: general – SubjectFull: Homogeneous catalysis Type: general – SubjectFull: Chemical derivatives Type: general Titles: – TitleFull: Diastereoselective Synthesis of an Industrially Relevant 4-Aminopentanoic Acid by Asymmetric Catalytic Hydrogenation in a Biphasic System Using Aqueous Sodium Hydroxide as Substrate Phase. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Piscopo, Calogero G. – PersonEntity: Name: NameFull: Gallou, Fabrice – PersonEntity: Name: NameFull: Leitner, Walter – PersonEntity: Name: NameFull: Franciò, Giancarlo IsPartOfRelationships: – BibEntity: Dates: – D: 15 M: 01 Text: 2017 Type: published Y: 2017 Identifiers: – Type: issn-print Value: 00397881 Numbering: – Type: volume Value: 49 – Type: issue Value: 2 Titles: – TitleFull: Synthesis Type: main |
| ResultId | 1 |
