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Title: A novel bifunctional allyldisilane as a triple allylation reagent in the stereoselective synthesis of trisubstituted tetrahydrofurans
Authors: Malkov, Andrei V.
Kysilka, Ondrej
Edgar, Mark
Kadlcikova, Aneta
Kotora, Martin
Kocovsky, Pavel
Keywords: Allylation
Asymmetric catalysis
Rearrangement
Silanes
Stereoselectivity
Issue Date: 2011
Publisher: © Wiley-VCH Verlag 7162 GmbH&Co. KGaA, Weinheim
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
Abstract: 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.
Description: 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
Sponsor: 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.
Version: Accepted for publication
DOI: 10.1002/chem.201100513
URI: https://dspace.lboro.ac.uk/2134/13545
Publisher Link: http://dx.doi.org/10.1002/chem.201100513
ISSN: 0947-6539
Appears in Collections:Closed Access (Chemistry)

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