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: v.aggarwal
bristol.ac.uk
E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett., 2009, 11, 165-168.
DOI: 10.1021/ol802651b
see article for more reactions
Abstract
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.
see article for more examples
Key Words
1,2-Diols, Hydroxylation, Hydrogen Peroxide
ID: J54-Y2009-0090
