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A novel bifunctional allyldisilane as a triple allylation reagent in the stereoselective synthesis of trisubstituted tetrahydrofurans

journal contribution
posted on 12.11.2013 by Andrei Malkov, Ondrej Kysilka, Mark Edgar, Aneta Kadlcikova, Martin Kotora, Pavel Kocovsky
Three for the price of two: A bifunctional allyldisilane undergoes a two-step triple allylation sequence with pairs of aldehydes to give all-cis trisubstituted tetrahydrofurans in excellent enantio- and diastereoselectivity (see scheme). The first allylation step, which sets up the key stereogenic centres, is catalysed by a chiral Lewis base.

Funding

The authors thank the University of Glasgow for a fellowship to O.K., the EPSRC for grant No. GR/S87294/01, MSˇMT for grant No. MSˇ M 002162857 and GACˇ R for grant No. P207/11/0587.

History

School

  • Science

Department

  • Chemistry

Citation

MALKOV, A.V. ... et al, 2011. A novel bifunctional allyldisilane as a triple allylation reagent in the stereoselective synthesis of trisubstituted tetrahydrofurans. Chemistry- A European Journal, 17 (26), pp. 7162 - 7166

Publisher

© Wiley-VCH Verlag 7162 GmbH&Co. KGaA, Weinheim

Version

AM (Accepted Manuscript)

Publication date

2011

Notes

This article is closed access, it was published in the serial Chemistry: A European Journal [© Wiley-VCH Verlag 7162 GmbH&Co. KGaA, Weinheim]. The definitive version is available at: http://dx.doi.org/10.1002/chem.201100513

ISSN

0947-6539

Language

en

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