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


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.

DOI: 10.1021/ja2066169

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@article{Saadi2011RapidOS, title={Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.}, author={Jakub Saadi and Matsujiro Akakura and Hisashi Yamamoto}, journal={Journal of the American Chemical Society}, year={2011}, volume={133 36}, pages={14248-51} }