Boyapati M. Choudary et al.
COMMUNICATIONS
layers were washed with 2 M aqueous NaOHsolution, if
CH3SO2NH2 was used. After removing the solvent, the crude
material was chromatographed on silica gel with EtOAc/
hexane to afford the corresponding cis-diol. The ee values of
the derivatized diols were determined by HPLC analysis using
Chiralcel OD-Hcolumn.
[3] a) C. Dobler, G. Mehltretter, M. Beller, Angew. Chem.
Int. Ed. Engl. 1999, 38, 3026 3028; b) C. Dobler, G. M.
Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem.
Soc. 2000, 122, 10289 10297.
[4] Review: a) C. Bolm, A. Gerlach, Eur. J. Org. Chem. 1998,
1, 21 27; b) P. Salvadori, D. Pini, A. Petri, Synlett 1999,
1181 1190.
[5] For polymer supported chiral ligands see: a) B. M. Kim,
K. B. Sharpless, Tetrahedron Lett. 1990, 31, 3003 3006;
b) D. Pini, A. Petri, A. Nardi, C. Rosini, P. Salvadori,
Tetrahedron Lett. 1991, 32, 5175 5178; c) H. Han, K. D.
Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731 1733.
[6] For achiral ligand-osmium tetroxide, see: a) G. Cainelli,
M. Contento, F. Manescalchi, L. Plessi, Synthesis 1989,
45 46; b) W. A. Herrmann, R. M. Kratzer, J. Bl¸mel,
H. B. Friedrich, R. W. Fischer, D. C. Apperley, J. Mink, O.
Berkesi, J. Mol. Catal. 1997, 120, 197 205.
Acknowledgements
K. Jyothi thanks the Indian Institute of Chemical Technology,
India for the award of a research fellowship and S. M. thanks the
Council of Scientific and Industrial Research, India for the
award of a senior research fellowship.
References and Notes
[7] For microencapsulated osmium tetroxide, see: a) S. Na-
gayama, M. Endo, S. Kobayashi, J. Org. Chem. 1998, 63,
6094 6095; b) S. Kobayashi, M. Endo, S. Nagayama, J.
Am. Chem. Soc. 1999, 121, 11229 11230; c) T. Ishida, R.
Akiyama, S. Kobayashi, Adv. Synth. Catal. 2003, 345,
576 579.
[8] S. Kobayashi, T. Ishida, R. Akiyama, Org. Lett. 2001, 3,
2649 2652.
[9] a) B. M. Choudary, N. S. Chowdari, M. L. Kantam, K. V.
Raghavan, J. Am. Chem. Soc. 2001, 123, 9220 9221;
b) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L.
Kantam, J. Am. Chem. Soc. 2002, 124, 5341 5345.
[1] a) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless,
Chem. Rev. 1994, 94, 2483 2547; b) I. E. Marko, J. S.
Svendsen, in Comprehensive Asymmetric Catalysis Vol. II,
(Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer,
Berlin, 1999, pp. 723 787; c) K. Bergstad, S. Y. Jonsson,
J.-E. Backvall, J. Am. Chem. Soc. 1999, 121, 10424 10425;
d) J. S. M. Wai, I. E. Marko, J. S. Svendsen, M. G. Finn,
E. N. Jacobsen, K. B. Sharpless, J. Am. Chem. Soc. 1989,
111, 1123 1125; e) A. Severeyns, D. E. De Vos, L.
Fireman, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew.
Chem. Int. Ed. 2001, 40, 586 589.
[2] H. Becker, K. B. Sharpless, Angew. Chem. Int. Ed. Engl.
1996, 35, 448 451.
1192
¹ 2003 WILEY-VCHVerlag GmbH& Co. KGaA, Weinheim
asc.wiley-vch.de
Adv. Synth. Catal. 2003, 345, 1190 1192