Abstract
Several sulfoxides with high enantiomeric purity have been synthesised using heterogeneous catalytic systems. A variety of titanium catalysts supported on Al2O3, SiO2, ZrO2 and montmorillonite, pillared clay catalysts using montmorillonite obtained from different sources and various chiral auxiliaries in presence of stoichiometric amounts of tertiary butyl hydroperoxide (TBHP) have been evaluated in asymmetric oxidation of prochiral sulfides to sulfoxides. It was found that Ti-PILC using montmorillonite K10 afforded optimum results. A probable active species responsible for high enantioselectivity is also discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. Mikolajczyk and J. Drawbowicz, Top. Stereo Chem. 13 (1982) 333.
G. Solladie, Synthesis (1981) 185.
G.H. Posner, in:The Chemistry in Sulfones and Sulfoxides, eds. S. Patai, Z. Rapport and C.J.M. Stirling (1988) 823.
E.J. Corey, L.O. Weigel, A.R. Chamberlin, H. Cho and D.H. Hua, J. Am. Chem. Soc. 102 (1980) 6613.
G. Solladie and F. Matloubi-Moghadam, J. Org. Chem. 47 (1982) 91.
A.J. Walker, Tetrahedron Asymmetry 3 (1992) 961, and references therein.
P. Pitchen, E. Dunach, M.N. Deshmukh and H.B. Kagan, J. Am. Chem. Soc. 106 (1984) 8188.
F. DiFuria, G. Modena and R. Seraglia, Synthesis (1984) 325.
S.H. Zhao, O. Samuel and H.B. Kagan, Tetrahedron 43 (1987) 5135.
H.U. Blaser, Tetrahedron Asymmetry 2 (1991) 843.
B.M. Choudary and V.L.K. Valli, J. Chem. Soc. Chem. Commun. (1990) 1115.
B.M. Choudary, V.L.K. Valli and A. Durga Prasad, J. Chem. Soc. Chem. Commun. (1990) 721.
B.M. Choudary and S. Shobha Rani, J. Mol. Catal. 75 (1992) L7.
B.M. Choudary, S. Shobha Rani and Y.V. Subba Rao,Proc. 10th Int. Congr. on Catalysis, Budapest 1992, eds. L. Guczi, F. Solymosi and P. Tétényi (Elsevier, Amsterdam).
A.M. Posner and J.P. Quirk, Proc. Roy. Soc. A 35 (1964) 278.
S. Yamanaka, T. Nishihara and M. Hattari, Mater. Chem. Phys. 17 (1987) 87.
J.R. Sohn and H.J. Jang, J. Catal. 136 (1992) 267.
B.M. Reddy, K. Narsimha, P.K. Rao and V.M. Mastikhin, J. Catal. 22 (1989) 118.
M. Deshmukh, E. Dunach, S. Juge and H.B. Kagan, Tetrahedron Lett. (1984) 3467.
M. Crocker and R.H.M. Herold, J. Mol. Catal. 70 (1991) 209.
M.G. Finn and K.B. Sharpless, J. Am. Chem. Soc. 113 (1991) 113.
Author information
Authors and Affiliations
Additional information
IICT communication No. 3189.
Rights and permissions
About this article
Cite this article
Choudary, B.M., Shobha Rani, S. & Narender, N. Asymmetric oxidation of sulfides to sulfoxides by chiral titanium pillared montmorillonite catalyst. Catal Lett 19, 299–307 (1993). https://doi.org/10.1007/BF00767071
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00767071