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Dynamic kinetic resolution in the asymmetric synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane
journal contribution
posted on 2013-11-12, 14:36 authored by Andrei MalkovAndrei Malkov, Sigitas Stoncius, Kvetoslava Vrankova, Matthias Arndt, Pavel KocovskyA 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.
Funding
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.
History
School
- Science
Department
- Chemistry
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 - 8085Publisher
© Wiley-VCH Verlag GmbH&Co. KGaA, WeinheimVersion
- AM (Accepted Manuscript)
Publication date
2008Notes
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.200801244ISSN
0947-6539eISSN
1521-3765Publisher version
Language
- en