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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, 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.
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.