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Rapid, one-pot synthesis of ?-siloxy-?-haloaldehydes.

ABSTRACT: The Mukaiyama cross-aldol reaction of ?-fluoro-, ?-chloro-, and ?-bromoacetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-?-siloxy-?-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel ?,?-bissiloxy-?,?-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.

SUBMITTER: Saadi J 

PROVIDER: S-EPMC3181128 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Saadi Jakub J   Akakura Matsujiro M   Yamamoto Hisashi H  

Journal of the American Chemical Society 20110818 36

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. ...[more]

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