A novel bifunctional allyldisilane as a triple allylation reagent in the stereoselective synthesis of trisubstituted tetrahydrofurans
Andrei Malkov
Ondrej Kysilka
Mark Edgar
Aneta Kadlcikova
Martin Kotora
Pavel Kocovsky
2134/13545
https://repository.lboro.ac.uk/articles/journal_contribution/A_novel_bifunctional_allyldisilane_as_a_triple_allylation_reagent_in_the_stereoselective_synthesis_of_trisubstituted_tetrahydrofurans/9395759
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.
2013-11-12 14:27:15
Allylation
Asymmetric catalysis
Rearrangement
Silanes
Stereoselectivity
Chemical Sciences not elsewhere classified