Volume 2007, Issue 5 p. 826-830
Full Paper

Enantiopure (9-Anthryl)(2-piperidyl)- and (9-Anthryl)(2-pyridyl)methanols – Their Use as Chiral Modifiers for Heterogeneous Hydrogenation of Keto Esters over Pt/Al2O3

Arlette Solladié-Cavallo

Arlette Solladié-Cavallo

Laboratoire de Stéréochimie Organométallique, ECPM/Université Louis Pasteur, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France, Fax: +33-3-90242706

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Claire Marsol

Claire Marsol

Laboratoire de Stéréochimie Organométallique, ECPM/Université Louis Pasteur, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France, Fax: +33-3-90242706

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Khalid Azyat

Khalid Azyat

Laboratoire de Stéréochimie Organométallique, ECPM/Université Louis Pasteur, 25 rue Becquerel, 67087 Strasbourg Cedex 02, France, Fax: +33-3-90242706

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Marin Roje

Marin Roje

Laboratory for Stereoselective Catalysis and Biocatalysis, Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia

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Christopher Welch

Christopher Welch

Merck & Co., Inc., Rahway, NJ 07065, USA

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Jennifer Chilenski

Jennifer Chilenski

Merck & Co., Inc., Rahway, NJ 07065, USA

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Philippe Taillasson

Philippe Taillasson

Sylachim-Finorga, 38670 Chasse sur Rhone, France

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Hugues D'Orchymont

Hugues D'Orchymont

Sanofi-Synthelabo Recherche, 67080 Strasbourg, France

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First published: 22 January 2007
Citations: 9

Graphical Abstract

Abstract

A route toward the synthesis of the erythro isomer of (9-anthryl)(2-piperidyl)methanol is presented as well as resolution and assignment of the structure (through NMR). The use of both the erythro and threo enantiopure isomers of this new amino alcohol, and its precursor [(9-anthryl)(2-pyridyl)methanol], as chiral modifiers for the Pt/Al2O3 hydrogenation of ethyl lactate showed that the erythro isomer is not necessarily the most efficient chiral modifier. This is probably because of the 9-anthryl group. The enantioselectivities that this compound provides are not, as one would expect, higher than those observed with the naphthyl group.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)