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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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Bibliographic Details
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.
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]
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Database: Engineering Source
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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]
ISSN:00397881
DOI:10.1055/s-0036-1588910