Communication
Organic & Biomolecular Chemistry
11 M. P. Bousquet, R. M. Willemot, P. Monsan and E. Boures,
Conclusions
J. Mol. Catal. B: Enzym., 1998, 5, 49.
In summary, a mild and highly efficient method has been 12 For kinetic resolutions see: (a) F. F. Huerta, Y. R. S. Laxmi and
developed for the direct synthesis of α-hydroxy acids from
monosubstituted ethylene glycols. Intriguingly, our studies
have shown that the solvent, pH and reaction temperature are
very vital for the success of this TEMPO mediated oxidation of
vicinal diol to α-hydroxy acid. Under the reaction conditions,
optically active glycol furnishes the corresponding α-hydroxy
J.-E. Backvall, Org. Lett., 2000, 2, 1037; (b) L. Tang and L. Deng,
J. Am. Chem. Soc., 2002, 124, 2870. For enzymatic resolutions
see: (c) H.-R. Huang, J.-H. Xu, Y. Xu, J. Pan and X. Liu, Tetra-
hedron: Asymmetry, 2005, 16, 2113; (d) R. F. Campbell,
K. Fitzpatrick, T. Inghardt, O. Karlsson, K. Nilsson, J. E. Reilly
and L. Yet, Tetrahedron Lett., 2003, 44, 5477.
acid in excellent yield with a high degree of optical purity. 13 (a) M.-X. Wang, G. Lu, G.-J. Ji, Z.-T. Huang, O. Meth-Cohn
Several functional groups such as –NO2, –F, –OBn, –OMs, –N3
and isopropylidene acetal are found to be stable under the
reaction conditions. Moreover, the catalytic version of this oxi-
dation is found to be equally efficient. Since this reagent com-
bination is more reliable and compatible with many functional
groups, this method will find wide application in organic
synthesis.22
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Acknowledgements
The authors thank DST and CSIR, India, for financial support
and DST-FIST for providing instrument facilities. KC thanks
UGC-New Delhi for a research fellowship.
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