Previously we have explored a new function of silylated alkynes conjugated with a carbonyl group and reported a carbon-carbon bond forming reaction via a consecutive activation step of conjugated alkynes involving an intramolecular migration of the silyl group.
Herein we report a novel reaction of silylated conjugate olefin and aldehyde mediated by tri-n-butylphosphine to afford silyl dienol ether via 1,4-Brook rearrangement reaction. We suppose the mechanism of the above reactions involves 1,4-addition of tri-n-butylphosphine followed by 1,4-Brook rearrangement, and subsequent Wittig reaction of resulting phosphonium ylides with aldehydes. We will present further studies of this reaction, including various substrates and aldehydes, and stereochemical control of the product.
