Skip to main content
SpringerLink
Log in

Stereochemistry of optically active compounds. Problems and prospects

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The review is concerned with the fundamental ideas and concepts of chiral stereochemistry, i.e., of the stereochemistry dealing with optically active compounds, from the asymmetric synthesis to the basics of mathematics, including characterization of the principal results and the current state of this branch of science.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. Meyer, Ber., 1888, 21, 789; 1890, 23, 568.

    Google Scholar 

  2. J. H. van't Hoff, Die Lagerung der Atome im Raume, Vieweg, Braunschweig, 1908.

    Google Scholar 

  3. M. A. Hantzch, La Stéréochimie, Génève, 1896.

  4. G. Wittig, Stereochimie, 1930.

  5. Stereochemie, Ed. K. Freudenberg, Deuticke Verlag, Leipzig, 1933.

    Google Scholar 

  6. S. Goldschmidt, Stereochemie, Akad. Verlag, Leipzig, 1933.

    Google Scholar 

  7. P. D. Ritchie, Asymmetric Synthesis and Asymmetric Induction, Oxford University Press, London, 1933.

    Google Scholar 

  8. E. S. Khotinskii, Stereokhimiya [Stereochemistry], Izd-vo Kharkovskogo Universiteta, Kharkov, 1950 (in Russian).

    Google Scholar 

  9. A. P. Terent'ev and V. M. Potapov, Osnovy stereokhimii [Fundamentals of Stereochemistry], Khimiya, Moscow, 1964 (in Russian).

    Google Scholar 

  10. K. Mislow, Introduction to Stereochemistry, W. A. Benjamin, New York, 1965.

    Google Scholar 

  11. E. L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962.

    Google Scholar 

  12. G. V. Bykov, Istoriya stereokhimii organicheskikh reaktsii [History of Stereochemistry of Organic Reactions], Nauka, Moscow, 1966 (in Russian).

    Google Scholar 

  13. V. M. Potapov, Stereokhimiya [Stereochemistry], Khimiya, Moscow, 1976, 695 pp. (in Russian).

    Google Scholar 

  14. V. I. Sokolov, Vvedenie v teoreticheskuyu stereokhimiyu [Introduction to Theoretical Stereochemistry], Nauka, Moscow, 1979; 2nd Ed., 1982 (in Russian).

    Google Scholar 

  15. M. Nogradi, Stereochemistry, Basic Concepts and Applications, Akademiai Kiado, Budapest, 1981, 283 pp.

    Google Scholar 

  16. W. J. Alworth, Stereochemistry and Its Application in Biochemistry, Wiley, New York, 1972.

    Google Scholar 

  17. V. I. Sokolov, Introduction to Theoretical Stereochemistry, Gordon & Breach, London, 1991 (extended and updated).

    Google Scholar 

  18. P. Maitland and W. H. Mills, Nature, 1935, 135, 994.

    Google Scholar 

  19. W. H. Perkin, W. J. Pope, and O. Wallach, J. Chem. Soc., 1909, 95, 1789.

    Google Scholar 

  20. W. H. Mills and C. R. Nodder, J. Chem. Soc., 1920, 117, 1407.

    Google Scholar 

  21. G. H. Christie and J. Kenner, J. Chem. Soc., 1922, 121, 614.

    Google Scholar 

  22. A. Luttringhaus and H. Gralheer, Naturwiss., 1940, 28, 255.

    Google Scholar 

  23. J. Meisenheimer, Liebiegs Ann. Chem., 1926, 449, 191.

    Google Scholar 

  24. J. Kenyon and H. Phillips, J. Chem. Soc., 1928, 3000.

  25. V. Prelog and P. Wieland, Helv. Chim. Acta, 1944, 27, 1127.

    Google Scholar 

  26. P. Crabbe, Top. Stereochem., 1976, 1, 1.

    Google Scholar 

  27. L. A. Tchugaev, Trans. Faraday Soc., 1914, 10, 70.

    Google Scholar 

  28. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca, New York, 1953, Chapter 7.

    Google Scholar 

  29. L. Rosenfeld, Z. Physik, 1928, 52, 161.

    Google Scholar 

  30. E. U. Condon, W. Altar, and H. Eyring, J. Chem. Phys., 1973, 5, 753.

    Google Scholar 

  31. W. Moffitt, R. D. Fitts, and J. G. Kirkwood, Proc. Natl. Acad. Sci., 1957, 43, 723, 1046.

    Google Scholar 

  32. J. A. Schellman, Acc. Chem. Res., 1988, 1, 144.

    Google Scholar 

  33. A. Werner, Z. Anorg. Allg. Chem., 1893, 3, 267.

    Google Scholar 

  34. R. B. Woodward, M. Cava, W. D. Ollis, A. Hunger, H. V. Daeniker, and K. Schenker, J. Am. Chem. Soc., 1954, 76, 4749.

    Google Scholar 

  35. R. B. Woodward and W. E. von Doering, J. Am. Chem. Soc., 1954, 67, 860.

    Google Scholar 

  36. M. Gates and G. Tschudi, J. Am. Chem. Soc., 1950, 72, 4839; 1952, 74, 1109.

    Google Scholar 

  37. G. Anner and K. Miescher, Helv. Chim. Acta, 1948, 31, 2173.

    Google Scholar 

  38. W. S. Johnson, J. W. Petersen, and C. D. Gutsche, J. Am. Chem. Soc., 1947, 69, 2942.

    Google Scholar 

  39. R. B. Woodward, F. Sondheimer, D. Taul, K. Heusler, and W. M. McLamore, J. Am. Chem. Soc., 1952, 74, 4223.

    Google Scholar 

  40. W. S. Johnson, I. A. David, H. C. Dehm, R. J. Highet, E. W. Warnhoff, W. D. Wood, and E. T. Jones, J. Am. Chem. Soc., 1958, 80, 661.

    Google Scholar 

  41. E. Fischer, Ber., 1891, 24, 2683.

    Google Scholar 

  42. W. Marckwald, Ber., 1904, 37, 349.

    Google Scholar 

  43. A. McKenzie, J. Chem. Soc., 1904, 85, 1249.

    Google Scholar 

  44. D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc., 1952, 74, 5828.

    Google Scholar 

  45. V. Prelog, Helv. Chim. Acta, 1953, 36, 308.

    Google Scholar 

  46. M. Cherest, H. Felkin, and N. Prudent, Tetrahedron Lett., 1968, 219.

  47. E. I. Klabunovskii, Asimmetricheskii sintez [Asymmetric Synthesis], Goskhimizdat, Moscow, 1960 (in Russian).

    Google Scholar 

  48. W. Kuhn and E. Braun, Naturwiss., 1929, 17, 227.

    Google Scholar 

  49. W. Kuhn and E. Knopf, Z. Phys. Chem., 1930, 7B, 292.

    Google Scholar 

  50. Origin of Optical Activity in Nature, Ed. D. C. Walker, Elsevier, Amsterdam, 1979.

    Google Scholar 

  51. J. M. Bijvoet, A. F. Peerdeman, and A. J. van Bommel, Nature, 1951, 168, 271.

    Google Scholar 

  52. R. S. Cahn and C. K. Ingold, J. Chem. Soc., 1951, 612.

  53. H. Krebs, Die Trennung von Racematen auf chromatographischem Wege, Westdeutsche Verlag, Koln, 1956.

    Google Scholar 

  54. A Practical Approach to Chiral Separations by Liquid Chromatography, Ed. G. Subramanian, VCH, New York, 1994.

    Google Scholar 

  55. V. A. Davankov, in Complexation Chromatography, Ed. A. Cagniant, New York, Marcel Dekker, 1992, 197.

    Google Scholar 

  56. M. Raban and K. Mislow, Top. Stereochem., 1967, v. 2, Wiley, New York.

    Google Scholar 

  57. J. A. Berson and D. A. Ben-Efraim, J. Am. Chem. Soc., 1959, 81, 4083.

    Google Scholar 

  58. J. Jacques, A. Collet, and S. H. Wilen, Enantiomers, Racemates, and Resolutions, Krieger Publ. Co., Malabar, 1991.

    Google Scholar 

  59. F. Toda, K. Tanaka, Z. Stein, and I. Goldberg, J. Org. Chem., 1994, 59, 5749.

    Google Scholar 

  60. J. Cancelli, L. Lacombe, and A. Collet, J. Am. Chem. Soc., 1985, 107, 6993.

    Google Scholar 

  61. V. I. Sokolov and O. A. Reutov, Usp. Khim., 1965, 34, 3 [Russ. Chem. Rev., 1965, 34 (Engl. Transl.)].

    Google Scholar 

  62. H. Brunner, Adv. Organomet. Chem., 1980, 18, 151.

    Google Scholar 

  63. E. J. O'Connor, M. Kobayashi, H. G. Floss, and J. A. Gladysz, J. Am. Chem. Soc., 1987, 109, 4837.

    Google Scholar 

  64. D. Arigoni and E. L. Eliel, Top. Stereochem., 1969, 4, 127.

    Google Scholar 

  65. J. Luthy, J. Retey, and D. Arigoni, Nature, 1969, 221, 1214.

    Google Scholar 

  66. A. M. Valentine, B. Wilkinson, K. E. Liu, S. Komar-Panicucci, N. D. Priestley, P. G. Williams, H. Morimoto, H. G. Floss, and S. J. Lippard, J. Am. Chem. Soc., 1997, 119, 1818.

    Google Scholar 

  67. G. Lowe and S. J. Salamuru, J. Chem. Soc., Chem. Communs, 1984, 466.

  68. G. Lowe, Acc. Chem. Res., 1983, 16, 244.

    Google Scholar 

  69. G. E. McCasland and S. Proskow, J. Am. Chem. Soc., 1955, 77, 4688; 1956, 78, 5646.

    Google Scholar 

  70. A. C. Cope, C. R. Ganellin, H. W. Johnson, T. V. van Auken, and H. J. S. Winkler, J. Am. Chem. Soc., 1963, 85, 3276.

    Google Scholar 

  71. D. J. Cram and N. L. Allinger, J. Am. Chem. Soc., 1955, 77, 6289.

    Google Scholar 

  72. A. Lüttringhaus and G. Eyring, Ann., 1957, 604, 111.

    Google Scholar 

  73. G. Paiaro and A. Panunzi, J. Am. Chem. Soc., 1964, 86, 5148.

    Google Scholar 

  74. K. Schlögl, Pure Appl. Chem., 1970, 23, 413.

    Google Scholar 

  75. V. I. Sokolov, Chirality and Optical Activity in Organometallic Compounds, Gordon and Breach, London, 1991.

    Google Scholar 

  76. V. I. Sokolov, Zh. Obshch. Khim., 1967, 37, 2207 [J. Gen. Chem. USSR, 1967, 37 (Engl. Transl.)].

    Google Scholar 

  77. M. S. Newman and D. Lednicer, J. Am. Chem. Soc., 1956, 78, 4765.

    Google Scholar 

  78. H. Wynberg and M. B. Groen, J. Am. Chem. Soc., 1968, 90, 5339.

    Google Scholar 

  79. A. C. D. Newman and H. M. Powell, J. Chem. Soc., 1952, 3747.

  80. A. Collet, Tetrahedron, 1987, 43, 5725.

    Google Scholar 

  81. J. Irurre, J. Santamaria, and M. C. Gonzalez-Rego, Chirality, 1995, 7, 154.

    Google Scholar 

  82. B. L. Murr and L. W. Feller, J. Am. Chem. Soc., 1968, 90, 2966.

    Google Scholar 

  83. G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York-London, 1971.

    Google Scholar 

  84. R. L. Kornegay, H. L. Frisch, and E. Wasserman, J. Org. Chem., 1969, 34, 2030.

    Google Scholar 

  85. D. K. Mitchell and J.-P. Sauvage, Angew. Chem., Int. Ed., 1989, 28, 189.

    Google Scholar 

  86. J. C. Chambron, D. K. Mitchell, and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4625.

    Google Scholar 

  87. J. M. Hawkins and A. Meyer, Science, 1993, 260, 1918.

    Google Scholar 

  88. V. N. Drozd, N. S. Zefirov, V. I. Sokolov, and I. V. Stankevich, Zh. Org. Khim., 1979, 15, 1785 [J. Org. Chem. USSR, 1979, 15 (Engl. Transl.)].

    Google Scholar 

  89. K. Mislow and R. Bolstad, J. Am. Chem. Soc., 1955, 77, 6712.

    Google Scholar 

  90. N. S. Zefirov, V. N. Drozd, V. I. Sokolov, and I. V. Stankevich, Zh. Org. Khim., 1981, 17, 233 [J. Org. Chem. USSR, 1981, 17 (Engl. Transl.)].

    Google Scholar 

  91. P. G. Mezey, J. Math. Chem., 1992, 11, 27.

    Google Scholar 

  92. H. Zabrodsky, H. Peleg, and D. Avnir, J. Am. Chem. Soc., 1992, 114, 7843; 1993, 115, 8278.

    Google Scholar 

  93. V. E. Kuz'min and I. B. Stel'makh, Zh. Strukt. Khim., 1987, 28, 45, 50 [J. Struct. Chem. (USSR), 1987, 28 (Engl. Transl.)].

    Google Scholar 

  94. V. Prelog, Chem. in Britain, 1968, 4, 382; Usp. Khim., 1969, 38, 952 [Russ. Chem. Rev., 1969, 38 (Engl. Transl.)]; Nobel Lecture: Science, 1976, 193, 17.

    Google Scholar 

  95. Lord Kelvin, Baltimore Lectures, Clay and Sons, London, 1904, 436; 619.

    Google Scholar 

  96. R. W. Robinson, F. Harary, and A. T. Balaban, Tetrahedron, 1976, 32, 355.

    Google Scholar 

  97. G. Polya, Acta Math., 1937, 68, 145.

    Google Scholar 

  98. V. I. Sokolov, Zh. Strukt. Khim., 1976, 17, 743 [J. Struct. Chem. (USSR), 1976, 17 (Engl. Transl.)].

    Google Scholar 

  99. V. A. Nikanorov and V. I. Sokolov, in Chemical Graph Theory, Math. Chem. Series, 1992, 2, 155; Gordon and Breach, Basel, Switzerland.

    Google Scholar 

  100. H. Hirschmann and K. R. Hansen, Top. Stereochem., 1983, 14, 183.

    Google Scholar 

  101. V. Prelog and G. Helmchen, Helv. Chim. Acta, 1972, 55, 2581; 2612.

    Google Scholar 

  102. G. Helmchen, G. Haas, and V. Prelog, Helv. Chim. Acta, 1973, 56, 2255.

    Google Scholar 

  103. K. Mislow and J. Siegel, J. Am. Chem. Soc., 1984, 106, 3319.

    Google Scholar 

  104. S. Fujita, Bull. Chem. Soc. Jpn., 2000, 73, 2009.

    Google Scholar 

  105. F. A. L. Anet, S. S. Miura, J. Siegel, and K. Mislow, J. Am. Chem. Soc., 1983, 105, 1419.

    Google Scholar 

  106. M. Cinquini, F. Cozzi, F. Sannicolo, and A. Sironi, J. Am. Chem. Soc., 1988, 100, 4363.

    Google Scholar 

  107. K. Mislow and M. Raban, Top. Stereochem., 1967, 1.

  108. J. P. Sauvage, Acc. Chem. Res., 1990, 23, 319.

    Google Scholar 

  109. D. M. Walba, R. M. Richards, and B. C. Haltiwanger, J. Am. Chem. Soc., 1982, 104, 3219.

    Google Scholar 

  110. D. M. Walba, Tetrahedron, 1985, 41, 3161.

    Google Scholar 

  111. J. Simon, in Graph Theory and Topology in Chemistry, Ed. R. B. King and D. H. Rouvray, Elsevier, Amsterdam, 1987.

    Google Scholar 

  112. R. S. Cahn, C. K. Ingold, and V. Prelog, Experientia, 1956, 12, 81; Angew. Chem., Int. Ed., 1966, 5, 385.

    Google Scholar 

  113. V. Prelog and G. Helmchen, Angew. Chem., Int. Ed., 1982, 21, 567.

    Google Scholar 

  114. J. A. Pople, J. Am. Chem. Soc., 1980, 102, 4615.

    Google Scholar 

  115. T. Verbiest, M. Kauranen, A. Persoons, M. Ikonen, J. Kurkela, and H. Lemmetyinen, J. Am. Chem. Soc., 1994, 116, 9203.

    Google Scholar 

  116. H. L. Frisch and E. Wasserman, J. Am. Chem. Soc., 1961, 83, 3789.

    Google Scholar 

  117. H. Gerlach, Yu. A. Owtschinnikov, and V. Prelog, Helv. Chim. Acta, 1964, 47, 2288.

    Google Scholar 

  118. H. H. Jaffe and M. Orchin, Symmetry in Chemistry.

  119. J. Donohue, Kristallografiya, 1981, 26, 908 [Sov. Phys.-Crystallogr., 1981, 26 (Engl. Transl.)].

    Google Scholar 

  120. V. I. Sokolov, Zh. Strukt. Khim., 1985, 26, 158 [J. Struct. Chem. (USSR), 1985, 26 (Engl. Transl.)].

    Google Scholar 

  121. C. J. Hawkins, Absolute Configuration of Metal Complexes, Wiley, New York, 1971.

    Google Scholar 

  122. D. Kepert, Inorganic Stereochemistry, Springer, Berlin, 1982.

    Google Scholar 

  123. V. I. Sokolov, Koord. Khim., 1984, 10, 610 [Sov. J. Coord. Chem., 1984, 10 (Engl. Transl.)].

    Google Scholar 

  124. V. I. Minkin, R. M. Minyaev, I. I. Zakharov, and V. I. Avdeev, Zh. Org. Khim., 1978, 14, 3 [J. Org. Chem. USSR, 1978, 14 (Engl. Transl.)].

    Google Scholar 

  125. V. I. Sokolov, Zh. Org. Khim., 1999, 35, 1289 [Russ. J. Org. Chem., 1999, 35 (Engl. Transl.)].

    Google Scholar 

  126. V. I. Sokolov, Zh. Strukt. Khim., 1980, 24, 170 [J. Struct. Chem., USSR, 1980, 24 (Engl. Transl.)].

    Google Scholar 

  127. S. S. Tratch and N. S. Zefirov, J. Chem. Inf. Comput. Sci., 1999, 36, 450.

    Google Scholar 

  128. C. Djerassi, Optical Rotatory Dispersion, McGraw-Hill, New York-Toronto-London, 1960.

    Google Scholar 

  129. L. Velluz, M. Legrand, and M. Grosjean, Optical Circular Dichroism, Acad. Press, New York, 1965.

    Google Scholar 

  130. E. Charney, The Molecular Basis of Optical Activity: Optical Rotatory Dispersion and Circular Dichroism, Wiley-Interscience, Chichester, 1979.

    Google Scholar 

  131. Circular Dichroism: Principles and Applications, Eds. K. Nakanishi, N. Berova, and R. W. Woody, VCH Publ., New York, 1994.

    Google Scholar 

  132. A. Moscowitz, Tetrahedron, 1961, 13, 48.

    Google Scholar 

  133. W. Moffitt, R. B. Woodward, A. Moscowitz, W. Klyne, and C. Djerassi, J. Am. Chem. Soc., 1961, 83, 4013.

    Google Scholar 

  134. Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, Ed. G. Snatzke, Heyden and Son, London, 1967.

    Google Scholar 

  135. G. V. Shustov, A. V. Kachanov, V. A. Korneev, R. G. Kostyanovsky, and A. Rauk, J. Am. Chem. Soc., 1993, 115, 10267.

    Google Scholar 

  136. A. I. Scott and A. D. Wrixon, Tetrahedron, 1971, 27, 2339.

    Google Scholar 

  137. J. P. Riel and F. S. Richardson, Chem. Rev., 1986, 86, 1.

    Google Scholar 

  138. S. C. J. Mesners, E. Peeters, B. M. W. Langeveld-Voss, and R. A. J. Janssen, J. Am. Chem. Soc., 1996, 118, 4902.

    Google Scholar 

  139. N. A. Cherepkov and V. V. Kuznetsov, J. Chem. Phys., 1991, 95, 3046.

    Google Scholar 

  140. D. J. Caldwell and H. Eyring, The Theory of Optical Activity, Wiley, New York, 1971.

    Google Scholar 

  141. J. H. Brewster, J. Am. Chem. Soc., 1959, 81, 5475; 5483; 5493.

    Google Scholar 

  142. J. H. Brewster, Top. Stereochem., 1967, 2, 1.

    Google Scholar 

  143. V. I. Sokolov and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 1964, 394 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1964 (Engl. Transl.)].

  144. Optical Active Polymers, Ed. E. Selegny, Reidel, Boston, 1979.

    Google Scholar 

  145. G. Wulff, Angew. Chem., Int. Ed., 1989, 21, 37.

    Google Scholar 

  146. M. M. Green, C. Andreola, B. Munoz, and H. P. Reidy, J. Am. Chem. Soc., 1988, 110, 4063.

    Google Scholar 

  147. W. S. Zielinski and W. J. Stec, J. Am. Chem. Soc., 1977, 99, 8365.

    Google Scholar 

  148. F. Eckstein, Acc. Chem. Res., 1979, 12, 204.

    Google Scholar 

  149. D. A. Tomalia, Adv. Mater., 1994, 6, 529.

    Google Scholar 

  150. G. R. Newcome, C. N. Moorefield, and F. Vogtle, Dendritic Macromolecules, Concepts, Synthesis, Perspectives, VCH, Weinheim, 1996.

    Google Scholar 

  151. W. Schlenk, Jr., Liebigs Ann. Chem., 1973, 1145.

  152. F. Toda, H. Miyamoto, H. Koshima, and Z. Urbanczyk-Lipkowska, J. Org. Chem., 1995, 60, 2130.

    Google Scholar 

  153. S. Ohba, H. Hosomi, K. Tanaka, H. Miyamoto, and F. Toda, Bull. Chem. Soc. Jpn., 2000, 23, 2075.

    Google Scholar 

  154. F. Toda, Acc. Chem. Res., 1995, 28, 480.

    Google Scholar 

  155. K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025.

    Google Scholar 

  156. D. K. Kondepudi and G. W. Nelson, Phys. Rev. Lett., 1983, 50, 1023.

    Google Scholar 

  157. H. Kelkar and R. Hatz, Handbook of Liquid Crystals. Verlag Chemie: Deerfield, Florida, 1980.

    Google Scholar 

  158. J. Szeitli, Cyclodextrins and Their Inclusion Complexes, Akademiai Kiado, Budapest, 1982.

    Google Scholar 

  159. J. F. Stoddard and R. Zarzycki, Rec. Trav. Chim., 1988, 107, 515.

    Google Scholar 

  160. V. I. Sokolov, Metalloorg. Khim., 1988, 1, 25 [Organomet. Chem. USSR, 1988, 1, 20 (Engl. Transl.)].

    Google Scholar 

  161. I. Ugi, J. Dugundji, R. Kopp, and D. Marquarding, Perspectives in Theoretical Stereochemistry, Springer-Verlag, Berlin-Heidelberg, 1984.

    Google Scholar 

  162. E. Ruch, Angew. Chem., Int. Ed., 1977, 16, 65.

    Google Scholar 

  163. A. S. Dreiding and K. Wirth, Math. Chem. (MATCH), 1980, 8, 341.

    Google Scholar 

  164. A. Dress, A. Dreiding, and H. Haegi, Studies in Physical and Theoretical Chemistry, 1983, 23, 39.

    Google Scholar 

  165. H. Zabrodsky and D. Avnir, Adv. Molec. Struct. Res., 1995, 1, 1; JAI Press.

  166. New Developments in Molecular Chirality, Ed. P. G. Mezey, Kluwer, Dordrecht, the Netherlands, 1991.

    Google Scholar 

  167. L. L. Morozov, E. I. Fedin, and M. I. Kabachnik, Zh. Fiz. Khim., 1973, 47, 2193; 2200; 2210 [J. Phys. Chem. USSR, 1973, 47 (Engl. Transl.)].

    Google Scholar 

  168. R. B. King, Theoret. Chim. Acta, 1983, 63, 103.

    Google Scholar 

  169. V. I. Sokolov, Comp. Math. Appls., 1986, 12B, 547.

    Google Scholar 

  170. K. Mislow, A. Buda, and T. Auf der Heide, Angew. Chem., Int. Ed., 1992, 31, 989.

    Google Scholar 

  171. V. E. Kuz'min, Zh. Fiz. Khim., 1994, 68, 1037 [Russ. J. Phys. Chem., 1994, 68 (Engl. Transl.)].

    Google Scholar 

  172. S. E. Alikhanidi and V. E. Kuz'min, Zh. Strukt. Khim., 1999, 39, 547 [J. Struct. Chem. (Russ.), 1999, 39 (Engl. Transl.)].

    Google Scholar 

  173. V. I. Sokolov, Zh. Strukt. Khim., 1975, 16, 971 [J. Struct. Chem. (USSR), 1975, 16 (Engl. Transl.)].

    Google Scholar 

  174. V. I. Sokolov and I. V. Stankevich, Zh. Strukt. Khim., 1978, 19, 226 [J. Struct. Chem. (USSR), 1978, 19 (Engl. Transl.)].

    Google Scholar 

  175. E. Ruch, Acc. Chem. Res., 1972, 5, 49; E. Ruch, Usp. Khim., 1975, 44, 156 [Russ. Chem. Rev., 1975, 44 (Engl. Transl.)].

    Google Scholar 

  176. E. Ruch and A. Schonhofer, Theor. Chim. Acta (Berlin), 1965, 3, 291; 1968, 10, 91.

    Google Scholar 

  177. V. I. Sokolov, Math. Chem. (MATCH), 1985, 17, 1.

    Google Scholar 

  178. V. I. Sokolov, Zh. Strukt. Khim., 1985, 26, 3 [J. Struct. Chem. (USSR), 1985, 26 (Engl. Transl.)].

    Google Scholar 

  179. V. I. Sokolov, Zh. Org. Khim., 1975, 11, 661 [J. Org. Chem. USSR, 1975, 11 (Engl. Transl.)].

    Google Scholar 

  180. A. V. Shubnikov, Problema dissimmetrii material'nykh ob"ektov [Problem of Dissymmetry of Material Objects], Izd-vo AN SSSR, Moscow, 1961 (in Russian).

    Google Scholar 

  181. A. V. Shubnikov and V. A. Koptsik, Symmetry in Science and Art, Plenum Press, New York, 1974.

    Google Scholar 

  182. J. Brocas and R. Willem, J. Am. Chem. Soc., 1983, 105, 2217.

    Google Scholar 

  183. The Measurement of Symmetry and Chirality: Conceptual Aspects, Ed. D. H. Rouvray, Wiley, New York, 1997.

    Google Scholar 

  184. V. E. Kuz'min and A. G. Artemenko, Zh. Strukt. Khim., 1999, 39, 541 [J. Struct. Chem. (Russ.), 1999, 39 (Engl. Transl.)].

    Google Scholar 

  185. V. E. Kuz'min, I. B. Stel'makh, M. B. Bekker, and D. V. Pozigun, J. Phys. Org. Chem., 1992, 5, 295.

    Google Scholar 

  186. V. E. Kuz'min, V. A. Chelombit'ko, I. V. Yudanova, I. B. Stel'makh, and I. S. Rublev, Zh. Strukt. Khim., 1998, 39, 552 [J. Struct. Chem. (Russ.), 1998, 39 (Engl. Transl.)].

    Google Scholar 

  187. O. Katzenelson and D. Avnir, Chem. Eur. J., 2000, 6, 1346.

    Google Scholar 

  188. C. E. Dalglish, J. Chem. Soc., 1952, 47, 3940.

    Google Scholar 

  189. A. G. Ogston, Nature, 1948, 162, 963.

    Google Scholar 

  190. W. H. Pirkle and T. C. Pochapsky, Chem. Rev., 1989, 89, 347.

    Google Scholar 

  191. V. I. Sokolov and N. S. Zefirov, Dokl. Akad. Nauk SSSR, 1991, 319, 1382 [Dokl. Chem., 1991 (Engl. Transl.)].

    Google Scholar 

  192. Y. Pinto, Y. Salomon, and D. Avnir, J. Math. Chem., 1998, 23, 13.

    Google Scholar 

  193. R. B. Woodward, F. E. Bader, H. Bickel, A. J. Frey, and R. W. Kirstead, J. Am. Chem. Soc., 1956, 78, 2023.

    Google Scholar 

  194. E. E. van Tamelen, T. A. Spencer, D. S. Allen, and R. L. Orviz, J. Am. Chem. Soc., 1959, 81, 6341.

    Google Scholar 

  195. J. C. Sheehan and K. R. Henery-Logan, J. Am. Chem. Soc., 1959, 81, 3089.

    Google Scholar 

  196. W. A. Bolhofer, J. C. Sheehan, and E. L. A. Adams, J. Am. Chem. Soc., 1960, 82, 3437.

    Google Scholar 

  197. M. Strell, A. Kaloyanoff, and H. Koller, Angew. Chem., 1960, 72, 169.

    Google Scholar 

  198. R. B. Woodward, W. A. Ayer, J. M. Beaton, F. Bickelhaupt, R. Bonnett, P. Buchschacher, G. L. Closs, H. Dutler, J. Hannah, F. R. Hauck, S. Ito, A. Langemann, E. Le Goff, W. Leimgruber, W. Lwowski, J. Sauer, Z. Valenta, and H. Volz, J. Am. Chem. Soc., 1960, 72, 3800.

    Google Scholar 

  199. E. J. Corey, S. Kim, S. Yoo, K. C. Nicolaou, L. S. Melvin, D. J. Brunelle, J. R. Falck, E. J. Trybulski, R. Lett, and P. W. Sheldrake, J. Am. Chem. Soc., 1978, 100, 4620.

    Google Scholar 

  200. R. W. Armstrong, J.-M. Beau, S. H. Cheon, W. J. Christ, H. Fujioka, W. H. Ham, L. D. Hawkins, H. Jin, S. H. Kang, Y. Kishi, M. J. Martinelli, W. W. M. Whorter, M. Mizune, M. Nakata, A. E. Stutz, F. X. Talamas, M. Taniguchi, J. A. Tino, K. Ueda, J. Uenishi, J. B. White, and M. Yonaga, J. Am. Chem. Soc., 1989, 111, 7525; 7530.

    Google Scholar 

  201. R. Breslow, Chem. Soc. Rev., 1972, 1, 553.

    Google Scholar 

  202. J. D. Morrison and H. S. Mosher, Asymmetric Organic Reactions, Prentice-Hall, New Jersey, 1971.

    Google Scholar 

  203. Y. Izumi and A. Tai, Stereo-differentiating Reactions. Academic Press, New York, 1977.

    Google Scholar 

  204. E. I. Klabunovskii, Stereospetsificheskii kataliz [Stereospecific Catalysis], Nauka, Moscow, 1968 (in Russian).

    Google Scholar 

  205. E. J. Corey, Chem. Soc. Rev., 1971, 25, 455.

    Google Scholar 

  206. K. Adachi, K. Naemura, and M. Nakazaki, Tetrahedron Lett., 1968, 5467.

  207. M. Tichy and J. Sicher, Tetrahedron Lett., 1969, 4609.

  208. T. L. Chan, C. W. Hung, T. O. Man, and M. K. Leung, J. Chem. Soc., Chem. Commun., 1994, 1971.

  209. T. J. Katz and J. Pesti, J. Am. Chem. Soc., 1982, 104, 346.

    Google Scholar 

  210. C. O. Dietrich-Buchecker and J.-P. Sauvage, Angew. Chem., Int. Ed., 1989, 28, 189.

    Google Scholar 

  211. C. O. Dietrich-Buchecker and J.-P. Sauvage, in Bioorganic Chemistry Frontiers, Springer, Berlin-Heidelberg, 1991, 2, 197.

    Google Scholar 

  212. Acc. Chem. Res., 1996, 29 (Special Issue), 3, Ed. A. W. Czarnik.

  213. Chem. Rev., 1997, 97 (Special Issue), 2, Ed. J. Szostak.

  214. W. S. Johnson, S. Esher, and B. M. Metcalf, J. Am. Chem. Soc., 1976, 98, 1039.

    Google Scholar 

  215. A. Fischli, Chimia, 1976, 30, 4.

    Google Scholar 

  216. H. C. Brown and G. Zweifel, J. Am. Chem. Soc., 1961, 83, 486.

    Google Scholar 

  217. M. P. Doyle, M. Protopopova, P. Muller, D. Ene, and E. A. Shapiro, J. Am. Chem. Soc., 1994, 116, 8492.

    Google Scholar 

  218. T. Katsuki, Coord. Chem. Rev, 1995, 140, 189.

    Google Scholar 

  219. B. R. James, Homogeneous Hydrogenation, Wiley-Interscience, J. Wiley and Sons, New York-London-Sydney-Toronto, 1973.

    Google Scholar 

  220. T. Hayashi, M. Tajika, K. Tamao, and M. Kumada, J. Am. Chem. Soc., 1976, 98, 3718.

    Google Scholar 

  221. R. Urban, G. Eberle, D. Marquarding, and I. Ugi, Angew. Chem., Int. Ed., 1976, 15, 627.

    Google Scholar 

  222. M. Kitamura, S. Suga, K. Kawai, and R. Noyori, J. Am. Chem. Soc., 1986, 108, 6071.

    Google Scholar 

  223. J. C. Fiaud, Tetrahedron Lett., 1975, 3495.

  224. Yu. N. Belokon', Janssen Chimica Acta, 1992, 10, 2, 1.

    Google Scholar 

  225. W. Zhang, J. L. Leobach, S. R. Wilson, and E. N. Jacobsen, J. Am. Chem. Soc., 1990, 112, 2801.

    Google Scholar 

  226. Yu. N. Belokon', S. Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Khrustalev, V. S. Larichev, M. A. Moskalenko, M. North, C. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, and L. V. Yashkina, J. Am. Chem. Soc., 1999, 121, 3968.

    Google Scholar 

  227. A. I. Meyers, Pure Appl. Chem., 1979, 51, 1255.

    Google Scholar 

  228. V. I. Sokolov, L. L. Troitskaya, and O. A. Reutov, J. Organomet. Chem., 1979, 182, 537.

    Google Scholar 

  229. B. Feringa and H. Wynberg, J. Am. Chem. Soc., 1976, 98, 4894; J. Org. Chem., 1991, 46, 2547.

    Google Scholar 

  230. M. Nakazaki, K. Yamamoto, and M. Maeda, Chem. Lett., 1980, 1553.

  231. I. Ojima, Catalytic Asymmetric Synthesis, VCH Publishers, New York, 1993.

    Google Scholar 

  232. L. Horner, H. Siegel, and H. Buthe, Angew. Chem., Int. Ed., 1968, 7, 942.

    Google Scholar 

  233. W. S. Knowles and M. Sabacky, J. Chem. Soc., Chem. Communs, 1968, 1445.

  234. H. B. Kagan and T. P. Dang, J. Am. Chem. Soc., 1972, 94, 6429.

    Google Scholar 

  235. J. Retey and J. A. Robinson, Stereospecifity in Organic Chemistry and Enzymology, Verlag Chemie, Weinheim, 1982.

    Google Scholar 

  236. G. M. Whitesides and C.-H. Wong, Angew. Chem., Int. Ed., 1985, 24, 617.

    Google Scholar 

  237. A. M. Klibanov, Acc. Chem. Res., 1990, 23, 114.

    Google Scholar 

  238. C.-H. Wong, Pure Appl. Chem., 1995, 67, 1609.

    Google Scholar 

  239. J. D. Stewart, K. W. Reed, C. A. Martinez, J. Zhu, G. Chen, and M. M. Kayser, J. Am. Chem. Soc., 1998, 120, 3541.

    Google Scholar 

  240. P. G. Schultz, Angew. Chem., Int. Ed., 1989, 28, 1283.

    Google Scholar 

  241. K. D. Janda, S. J. Benkovic, and R. A. Lerner, Science, 1989, 244, 437.

    Google Scholar 

  242. R. Noyori, Chem. Soc. Rev., 1989, 18, 187.

    Google Scholar 

  243. W. S. Knowles, J. Chem. Educ., 1986, 63, 222.

    Google Scholar 

  244. T. Sakakura and T. Sato, Chem. Lett., 1997, 1089.

  245. M. J. Burk, S. Feng, M. F. Gross, and W. Tumas, J. Am. Chem. Soc., 1995, 117, 8277.

    Google Scholar 

  246. A. Stefani, G. Consiglio, C. Botteghi, and P. Pino, J. Am. Chem. Soc., 1973, 95, 6504.

    Google Scholar 

  247. M. Lautens, W. Tam, and C. Sood, J. Org. Chem., 1993, 58, 4513.

    Google Scholar 

  248. R. D. Broene and S. L. Buchwald, J. Am. Chem. Soc., 1993, 115, 12569.

    Google Scholar 

  249. G. W. Muller, Chem. Tech., January 1997, p. 21.

  250. EUCHEM Conference on Stereochemistry, Bürgenstock/Switzerland 1965–1989 Otto Salle Verlag, Frankfurt am Main und Verlag Sauerländer AG, Aarau, 1989.

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    V. I. Sokolov

Authors
  1. V. I. Sokolov
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sokolov, V.I. Stereochemistry of optically active compounds. Problems and prospects. Russian Chemical Bulletin 50, 1339–1355 (2001). https://doi.org/10.1023/A:1012735003500

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012735003500

Search

Navigation