Partial separation of enantiomeric 1,2-diols via ketal formation with a polymer-supported chiral ketone

Abstract

Partial separations of the (R,R)- and (S,S)-enantiomers of butane-2,3-diol, trans-cyclohexane-1,2-diol and dimethyl tartrate were achieved via ketal formation with a polymer-supported 7-keto steroid; in each case one enantiomer reacted in higher yield than the other and release of the diols from the support gave diol fractions significantly enriched in one enantiomer

References

1. (a) Polymer-supported Reactions in Organic Synthesis, ed. P. Hodge and D. C. Sherrington, Wiley, Chichester, 1980; (b) Syntheses and Separations Using Functional Polymers, ed. D. C. Sherrington and P. Hodge, Wiley, Chichester, 1988; (c) Polymeric Reagents and Catalysts, ed. W. T. Ford, ACS Symposium Series 308, Washington D.C., 1986.
2. R. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149.
3. P. Hodge, Chem. Ind., 1979, 624; J. M. J. Fréchet, ch. 6 in ref. 1(a).
4. G. Lowe, Chem. Soc. Rev., 1996, 25, 309.
5. N. K. Terrett, M. Gardner, D. W. Gordon, R. J. Kobylecki and J. Steele, Tetrahedron, 1995, 51, 8135.
6. P. Hodge and J. Waterhouse, J. Chem. Soc., Perkin Trans. 1, 1983, 2319.
7. E. Seymour and J. M. J. Fréchet, Tetrahedron Lett., 1976, 3669.
8. T. M. Fyles and C. C. Leznoff, Can. J. Chem., 1976, 54, 935.
9. M. J. Farrall and J. M. J. Fréchet, J. Org. Chem., 1976, 41, 3877.
10. H. R. Nace and G. A. Crosby, J. Org. Chem., 1979, 44, 3105.
11. D. H. R. Barton and J. D. Cox, J. Chem. Soc., 1948, 783.
12. H. C. Meuley, US Pat. 2 505 646, (Chem. Abstr., 1950, 44, 6894).
13. P. Hodge, J. Kemp, E. Khoshdel and G. M. Perry, Reactive Polymers, 1985, 3, 299.
14. Dictionary of Organic Compounds, 5th edn.,, Chapman and Hall, New York, 1982.