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In this communication, we report that substrate-controlled 1,5-syn and -anti stereoinduction in the aldol reaction of beta-tris(trialkylsilyl)siloxy methyl ketones can be achieved with high diastereoselectivities. Tris(trialkylsilyl)silyl groups are easily prepared and play an important role in the selectivities of these reactions. Furthermore, all of the 1,3,5-triol stereoisomers can easily be prepared from beta-siloxy methyl ketones in no more than three steps.

journal of the american chemical society

Super Silyl Stereo-Directing Groups for Complete 1,5-Syn and -Anti Stereoselectivities in the Aldol Reactions of β-Siloxy Methyl Ketones with Aldehydes