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A novel bifunctional allyldisilane as a triple allylation reagent in the stereoselective synthesis of trisubstituted tetrahydrofurans
journal contributionposted on 12.11.2013 by Andrei Malkov, Ondrej Kysilka, Mark Edgar, Aneta Kadlcikova, Martin Kotora, Pavel Kocovsky
Any type of content formally published in an academic journal, usually following a peer-review process.
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.
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.