A Method for the Preparation of Differentiated \(trans\)-1,2-Diol Derivatives with Enantio- and Diastereocontrol

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A Method for the Preparation of Differentiated \(trans\)-1,2-Diol Derivatives with Enantio- and Diastereocontrol

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Title: A Method for the Preparation of Differentiated \(trans\)-1,2-Diol Derivatives with Enantio- and Diastereocontrol
Author: Myers, Andrew G.; Lim, Sang Min; Hill, Nicholas

Note: Order does not necessarily reflect citation order of authors.

Citation: Lim, 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.
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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.
Published Version: doi:10.1021/ja901283q
Other Sources: http://www.chem.harvard.edu/groups/myers/page15/page15.html
Terms of Use: This article is made available under the terms and conditions applicable to Open Access Policy Articles, as set forth at http://nrs.harvard.edu/urn-3:HUL.InstRepos:dash.current.terms-of-use#OAP
Citable link to this page: http://nrs.harvard.edu/urn-3:HUL.InstRepos:5125262
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