Organocatalytic Asymmetric Vinylogous Aldol Reaction of Allyl Aryl Ketones to Silyl Glyoxylates

A direct
organocatalytic asymmetric vinylogous aldol reaction of
allyl aryl ketones to silyl glyoxylates has been developed through
the bifunctional catalyst, giving the α-hydroxysilanes with
excellent enantioselectivity (up to 95% ee) and in high yields (up
to 96%). The success of this catalytic methodology offers an opportunity
to tackle the problems in the nucleophilic addition to acylsilanes.
To activate both allyl aryl ketones and acylsilanes, the utilized
bifunctional catalyst was an ideal organocatalyst in this unprecedented
transformation.