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Design and synthesis of a heterogeneous asymmetric catalyst

Wan, Kam T. and Davis, Mark E. (1994) Design and synthesis of a heterogeneous asymmetric catalyst. Nature, 370 (6489). pp. 449-450. ISSN 0028-0836. https://resolver.caltech.edu/CaltechAUTHORS:20150514-094516560

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Abstract

The need for enantiomerically pure pharmaceuticals and insecticides drives the search for new catalysts that can perform asymmetric reactions with high enantiomeric selectivity. Many chiral transformations are accomplished using homogeneous catalysts. Recently we reported a heterogeneous catalyst for asymmetric hydrogenation reactions, in which an organometallic catalytic complex is held in a film of water on a porous hydrophilic support, while the reactants and products remain within a hydrophobic organic phase. Such systems provide a large interfacial area between the catalytic phase and the solvent, and should facilitate the separation of product from catalyst. Our previous system gave selectivities of only about 70% enantiomeric excess, however, whereas values of at least 95% are needed for practical utility. Here we describe a modified process in which an enantiomeric excess of 96% is obtained for the asymmetric reduction of 2-(6′-methoxy-2′-naphthyl)acrylic acid to the commercially important anti-inflammatory agent naproxen. We use ethylene glycol as the hydrophilic liquid phase containing the chiral catalyst, which effectively prevents the leaching of the complex into the organic phase. Our results show that these supported-phase asymmetric catalytic systems have the potential to become commercially viable.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1038/370449a0DOIArticle
http://www.nature.com/nature/journal/v370/n6489/abs/370449a0.htmlPublisherArticle
ORCID:
AuthorORCID
Davis, Mark E.0000-0001-8294-1477
Additional Information:© 1994 Nature Publishing Group. Received 27 April; accepted 28 June 1994. We thank D. Forster for a generous gift of 2-(6'-methoxy-2'-naphthyl)-acrylic acid. This work was supported by the US NSF Alan T. Waterman Award (M.E.D.).
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Issue or Number:6489
Record Number:CaltechAUTHORS:20150514-094516560
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150514-094516560
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57524
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:14 May 2015 18:24
Last Modified:09 Mar 2020 13:18

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