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Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols

Emeline Vedrenne, Olov A. Wallner, Maxime Vitale, Frank Schmidt and Varinder K. Aggarwal*

*School of Chemistry, University of Bristol, Bristol BS81TS, U.K, Email:

E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett., 2009, 11, 165-168.

DOI: 10.1021/ol802651b

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Lithiated epoxides react stereospecifically with boronates to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.

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Key Words

1,2-Diols, Hydroxylation, Hydrogen Peroxide

ID: J54-Y2009-0090