Multicomponent Hosomi–Sakurai reaction on chiral, bio-based, alcohols†

Abstract

The multicomponent Hosomi–Sakurai reaction, which gives homoallyl ethers from aldehydes, trimethylsilyl ethers and allyltrimethylsilane, was thoroughly studied using a bio-based aldehyde (protected 5-(hydroxymethyl)tetrahydrofuran-2-carboxyaldehyde) along with trimethylsilyl ethers derived from a variety of (mainly bio-based) alcohols. For comparison, a reactive aromatic aldehyde was also employed. These studies helped to identify the optimal conditions for each aldehyde and provided insight into the scope and limitations of this relatively underexplored multicomponent reaction, one of the few that can incorporate alcohols as diversity inputs.