Abstract
Allylic silanes bearing a silylmethyl group at the allylic position
were prepared as both (E )- and (Z )-alkene stereoisomers. These compounds
undergo reactions with aldehydes in the presence of Lewis acids
to provide tetrahydrofurans, bearing up to five stereogenic centers,
as single diastereomers. These annulation processes are likely facilitated
because the reactions proceed via carbocations that are stabilized
by two β-silyl substituents.
Key words
tetrahydrofurans - silylmethyl allylic silanes - annulation
reaction - rearangements
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