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Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

ABSTRACT: 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.

SUBMITTER: Yamaoka Y

PROVIDER: S-EPMC2868325 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

Yamaoka Yousuke Y Yamamoto Hisashi H

Journal of the American Chemical Society 20100401 15

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. ...[more]

PMID: 20349994

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