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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 12.11.2013 by Andrei Malkov, Sigitas Stoncius, Kvetoslava Vrankova, Matthias Arndt, Pavel Kocovsky
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.

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 - 8085

Publisher

© Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim

Version

AM (Accepted Manuscript)

Publication date

2008

Notes

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

ISSN

0947-6539

eISSN

1521-3765

Language

en

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