Silica gel supported bis-cinchona alkaloid derivatives and a pre

Details Silica gel supported bis-cinchona alkaloid derivatives and a pre Silica gel supported bis-cinchona alkaloid derivatives and a pre

1998-03-26

1999-10-19

Bell, Mark L.

Catalyst, solid sorbent, or support therefor: product or process

Catalyst or precursor therefor

Organic compound containing

502151, 502158, 502167, 502233, B01J 3100, B01J 2108, B01J 2112, B01J 2114

Patent

active

059688670

ABSTRACT:
The present invention relates to silica gel supported bis-cinchona alkaloid compounds of the formula: ##STR1## wherein Q is dihydroquininyl or dihydroquinindinyl; X is a compound having 4 carbon atoms; and R is methoxy, ethoxy or methyl; and methods of preparation and use thereof. The silica gel supported bis-cinchona alkaloid derivatives of this invention are useful re-useable catalysts for preparing vicinal diols by asymmetric dihydroxylation of olefins.

REFERENCES:
R. A. Johnson et al, "Catalytic Asymmetric Dihydroxylation" in Catalytic Asymmetric Synthesis, I. Ojima ed., VCH Publishers, New York, pp. 227-272, (1993).
H.C. Kolb et al, "Catalytic Asymmetric Dihydroxylation", Chem. Rev., 94, pp. 2483-2547 (1994).
B.B. Lohray, "Recent Advances in the Asymmetric Dihyroxylation of Alkenes", Tetrahedron: Asymmetry, vol. 3, No. 11, pp. 1317-1349, (1992).
B.M. Kim et al., "Heterogeneous Catalytic Asymmetric Dihydroxylation: Use of a Polymer-Bound Alkaloid", Tetrahedron Letters, vol. 31, No. 21, pp. 3003-3006, (1990).
D. Pini, et al., "Heterogeneous Catalytic Asymmetric Dihydroxylation of Olefins with the OsO.sub.4 /Poly(9-O-Acylquinine-co-Acrylonitrile) System", Tetrahedron Letters, vol. 32, No. 38, pp. 5175-5178, (1991).
D. Pini et al, "A New Crosslinked Polymer for the Heterogeneous Catalytic Asymmetric Dihydroxylation of Alkenes", Tetrahedron: Asymmetry, vol. 4, No. 11, pp. 2351-2354 (1993).
B.B. Lohray et al, "Unprecedented Reactivity and Selectivity in Hetrogeneous Asymmetric Catalytic Dihydroxylation of Alkenes", Tetrahedron Letters, vol. 35, No. 35, pp. 6559-6562 (1994).
C. Rosini et al., "Cinchona Alkaloids for Preparing New, Easily Accessible Chiral Stationary Phases", Journal of Chromatography, 348, pp. 79-87 (1985).

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