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Issue 2, 2007
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Enantioselective synthesis of β2-amino acids using rhodium-catalyzed hydrogenation

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Abstract

A series of protected β2-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained (up to 91%) with full conversion for a number of β-amino acids.

Graphical abstract: Enantioselective synthesis of β2-amino acids using rhodium-catalyzed hydrogenation

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Article information


Submitted
18 Oct 2006
Accepted
20 Nov 2006
First published
08 Dec 2006

Org. Biomol. Chem., 2007,5, 267-275
Article type
Paper

Enantioselective synthesis of β2-amino acids using rhodium-catalyzed hydrogenation

R. Hoen, T. Tiemersma-Wegman, B. Procuranti, L. Lefort, J. G. de Vries, A. J. Minnaard and B. L. Feringa, Org. Biomol. Chem., 2007, 5, 267
DOI: 10.1039/B615131K

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