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Asymmetric catalysis by chiral lanthanide complexes in water

Dickins, R.S.; Gaillard, S.; Hughes, S.P.; Badari, A.

Authors

R.S. Dickins

S. Gaillard

S.P. Hughes

A. Badari



Abstract

The development of catalytic, asymmetric transformations in water is a challenging task. The lanthanides are becoming reagents of choice for many Lewis acid-catalyzed reactions in aqueous media as they are water tolerant. However, enantioselective reactions catalyzed by lanthanides are difficult to achieve in water due to the instability of the reported catalysts. Herein we report the development of stable, well-defined chiral lanthanide complexes and their effectiveness in the asymmetric reduction of alpha-keto acids in aqueous solution. This is the first. example of asymmetric reduction by a chiral lanthanide complex in water. Although modest ees are obtained (40-50%) the ytterbium complexes offer a unique advantage as they have the ability to monitor, direct from the reaction mixture, the % ee for the reaction, by H-1 NMR, through a dipolar analysis of the observed paramagnetic shift.

Citation

Dickins, R., Gaillard, S., Hughes, S., & Badari, A. (2005). Asymmetric catalysis by chiral lanthanide complexes in water. Chirality, 17(7), 357-363. https://doi.org/10.1002/chir.20171

Journal Article Type Article
Publication Date 2005-06
Deposit Date Apr 20, 2007
Journal Chirality
Print ISSN 0899-0042
Electronic ISSN 1520-636X
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 17
Issue 7
Pages 357-363
DOI https://doi.org/10.1002/chir.20171
Keywords Asymmetric reduction, Aqueous solution, Ytterbium, paramagnetic NMR, Keto acids, Enantioselectivity.

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