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A method for the preparation of differentiated trans-1,2-diol derivatives with enantio- and diastereocontrol.

ABSTRACT: We describe a synthetic sequence that allows for the preparation of optically active trans-1,2-diol monosilyl ether derivatives from ketones, providing a new means for retrosynthetic simplification of differentiated diol and polyol targets. The sequence involves silyl enol ether formation, Shi asymmetric epoxidation, and then regio- and stereospecific addition of hydride, methide, or higher alkylide. The tactical combination presented has not been integrated in synthetic problem solving, so far as we are aware, but has promise for broad application.

SUBMITTER: Lim SM

PROVIDER: S-EPMC2681323 | biostudies-other | 2009 Apr

REPOSITORIES: biostudies-other

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A method for the preparation of differentiated trans-1,2-diol derivatives with enantio- and diastereocontrol.

Lim Sang Min SM Hill Nicholas N Myers Andrew G AG

Journal of the American Chemical Society 20090401 16

We describe a synthetic sequence that allows for the preparation of optically active trans-1,2-diol monosilyl ether derivatives from ketones, providing a new means for retrosynthetic simplification of differentiated diol and polyol targets. The sequence involves silyl enol ether formation, Shi asymmetric epoxidation, and then regio- and stereospecific addition of hydride, methide, or higher alkylide. The tactical combination presented has not been integrated in synthetic problem solving, so far ...[more]

PMID: 19341239

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