title: Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.
abstract: The Mukaiyama cross-aldol reaction of α-fluoro-, α-chloro-, and α-bromoacetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-β-siloxy-α-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel β,δ-bissiloxy-α,γ-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Jakub
authors.initials: J
authors.lastname: Saadi
authors.forename: Matsujiro
authors.initials: M
authors.lastname: Akakura
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000079:Acetaldehyde / Q000138:chemical synthesis*; D054879:Halogenation; D061065:Polyketides / Q000138:chemical synthesis*
chemical_list: D061065:Polyketides; D000079:Acetaldehyde