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Synthesis 2017; 49(02): 353-357
DOI: 10.1055/s-0036-1588910
paper
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of an Industrially Relevant 4-Aminopentanoic Acid by Asymmetric Catalytic Hydrogenation in a Biphasic­ System Using Aqueous Sodium Hydroxide as Substrate Phase

Calogero G. Piscopo
a   Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany
,
Fabrice Gallou
b   Novartis Pharma AG, Postfach, 4002 Basel, Switzerland   Email: francio@itmc.rwth-aachen.de   Email: leitner@itmc.rwth-aachen.de
,
Walter Leitner*
a   Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany
,
Giancarlo Franciò*
a   Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany
› Author Affiliations
Further Information

Publication History

Received: 17 October 2016

Accepted: 20 October 2016

Publication Date:
22 November 2016 (online)

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Dedicated to Prof. Dieter Enders on the occasion of his 70th birthday, in deep respect for his groundbreaking contributions to asymmetric catalysis.

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.

Key words

asymmetric hydrogenation - aqueous biphasic catalysis - ruthenium - Mandyphos - ionic liquid - catalyst immobilization

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588910.
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