Categories: C-O Bond Formation > Synthesis of esters > Esterification, Transesterification, Acylation >
Desymmetrizations of Diols
Recent Literature
A new class of anionic, boron-bridged analogues of the box ligands was
developed. These borabox ligands showed a considerable potential for
asymmetric cyclopropanation and desymmetrizations of meso diols.
C. Mazet, V. Koehler, A. Pfaltz, Angew. Chem. Int. Ed., 2005,
44, 4888-4891.
A copper complex of a novel alicyclic chiral C2-symmetric
piperazine allows the benzoylation of a series of cyclic and acyclic meso-1,2-diols
to give optically active monobenzoates with high enantioselectivity.
D. Nakamura, K. Kakiuchi, K. Koga, R. Shirai, Org. Lett., 2006,
8, 6139-6142.
A dinuclear asymmetric zinc catalyst has been applied for the desymmetrization of some meso diols.
The best
acyl transfer agent proved to be vinyl benzoate. Diacylation normally did not
occur. A model to rationalize the results is presented.
B. M. Trost, T. Mino, J. Am. Chem. Soc., 2003, 125, 2410-2411.
B. M. Trost, T. Mino, J. Am. Chem. Soc., 2003, 125, 2410-2411.
