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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, 14:27 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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