A Method for the Preparation of Differentiated \(trans\)-1,2-Diol Derivatives with Enantio- and Diastereocontrol
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CitationLim, Sang Min, Nicholas Hill, and Andrew G. Myers. 2009. A method for the preparation of differentiated \(trans\)-1,2-diol derivatives with enantio- and diastereocontrol. Journal of the American Chemical Society 131(16): 5763-5765.
AbstractWe 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.
Citable link to this pagehttp://nrs.harvard.edu/urn-3:HUL.InstRepos:5125262
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