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. 2016 Nov 18;18(22):5880-5883.
doi: 10.1021/acs.orglett.6b02959. Epub 2016 Nov 9.

Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation

Ignacio Colomer  1 , Rosimeire Coura Barcelos  1 , Kirsten E Christensen  1 , Timothy J Donohoe  1
Affiliations

Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation

Ignacio Colomer et al. Org Lett. .

Abstract

A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds.

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