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Site-selective catalysis: toward a regiodivergent resolution of 1,2-diols.

ABSTRACT: This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.

SUBMITTER: Worthy AD

PROVIDER: S-EPMC3342470 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Site-selective catalysis: toward a regiodivergent resolution of 1,2-diols.

Worthy Amanda D AD Sun Xixi X Tan Kian L KL

Journal of the American Chemical Society 20120419 17

This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step. ...[more]

PMID: 22515351

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