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A novel bifunctional allyldisilane as a triple allylation reagent in the stereoselective synthesis of trisubstituted tetrahydrofurans
journal contribution
posted on 2013-11-12, 14:27 authored by Andrei MalkovAndrei Malkov, Ondrej Kysilka, Mark Edgar, Aneta Kadlcikova, Martin Kotora, Pavel KocovskyThree 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 - 7166Publisher
© Wiley-VCH Verlag 7162 GmbH&Co. KGaA, WeinheimVersion
- AM (Accepted Manuscript)
Publication date
2011Notes
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.201100513ISSN
0947-6539Publisher version
Language
- en