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Title: Dynamic kinetic resolution in the asymmetric synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane
Authors: Malkov, Andrei V.
Stoncius, Sigitas
Vrankova, Kvetoslava
Arndt, Matthias
Kocovsky, Pavel
Keywords: Amino acids
Asymmetric synthesis
Issue Date: 2008
Publisher: © Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim
Citation: MALKOV, A.V. ... et al, 2008. Dynamic kinetic resolution in the asymmetric synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane. Chemistry - A European Journal, 14 (27), pp. 8082 - 8085
Abstract: A new methodology based on the organocatalytic asymmetric hydrosilylation of enamines that allows a direct access to a range of β and β -amino acid derivatives was presented. The results show a successful reduction of aromatic substrates, a sterically more hindered ortho-substituted derivatives, and the thiophenyl analogue exhibiting lower reactivity. Fast enamine-imine equilibration is crucial as imines are chiral but racemic, while α-alkyl β-amino acids can be accessed by the symmetrical Mannich reaction. The α-alkyl derivatives have relative and absolute configuration due to their reduction with LiAlH into a known amino alcohols. Predominant formation of the anti isomer in 3o is consistent with conformation of the imine intermediate in the catalytic reduction.
Description: This article is closed access, it was published in the serial Chemistry: A European Journal [© Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim]. The definitive version is available at: http://dx.doi.org/10.1002/chem.200801244
Sponsor: The authors thank the EPSRC for grant no. GR/S87294/01, the European Socrates- Erasmus Exchange Program for a fellowship to M.A., and the University of Glasgow for a fellowship to K.V.
Version: Accepted for publication
DOI: 10.1002/chem.200801244
URI: https://dspace.lboro.ac.uk/2134/13546
Publisher Link: http://dx.doi.org/10.1002/chem.200801244
ISSN: 0947-6539
Appears in Collections:Closed Access (Chemistry)

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