Nonlinear stereochemical effects in asymmetric reactions

Tetrahedron Asymmetry

Volumn 8, Issue 18, 1997, Pages 2997-3017

  Avalos, Martín ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Jiménez, José L ^a   Palacios, Juan C ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0030884481     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00375-3     Document Type: Review

References (96)

1. a) Mason, S. F. Molecular Optical Activity and the Chiral Discriminations Cambridge University Press, Cambridge, 1982.
2. b) Bonner, W. A. Top. Stereochem. 1988, 18, 1-96.
3. c) Inoue, Y. Chem. Rev. 1992, 92, 741-770.
4. a) Horeau, A. Tetrahedron Lett. 1969, 3121-3124.
5. b) Horeau, A.; Guetté, J. P. Tetrahedron 1974, 30, 1923-1931.
6. For an excellent and comprehensive survey on stereoisomer discrimination, properties of racemates and of their enantiomers: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds Wiley, New York, 1994, Chapter 6, pp. 153-295.
7. a) Wynberg, H.; Feringa, B. Tetrahedron 1976, 32, 2831-2834.
8. b) Wynberg, H.; Lorand, J. P. J. Org. Chem. 1981, 46, 2538-2542.
9. c) Okada, M.; Sumitomo, H.; Atsumi, M. J. Am. Chem. Soc. 1984, 106, 2101-2104.
10. d) Grassi, M.; Di Silvestro, G.; Farina, M. Tetrahedron 1985, 41, 177-181.
11. a) Kabachnik, M. I.; Mastryukova, T. A.; Fedin, E. I.; Vaisberg, M. S.; Morozov, L. L.; Petrovskii, P. V.; Shipov, A. E. Russ. Chem. Rev. 1978, 47, 821-844.
12. b) Dobashi, A.; Saito, N.; Motoyama, Y.; Hara, S. J. Am. Chem. Soc. 1986, 108, 307-308.
13. Luchinat, C.; Roelens, S. J. Am. Chem. Soc. 1986, 108, 4873-4878.
14. From now on we will use the acronym NLE to denote a nonlinear stereochemical effect. Do not confuse this term with NLO (nonlinear optical effect), which has been largely popularized and states that molecules with large hyperpolarizabilities are liable to have nonlinear optical properties.
15. There are numerous and excellent reviews on catalytic asymmetric reactions, some of them describing examples of NLEs: a) Kagan, H. B. Bull. Soc. Chim. Fr. 1988, 846-853.
16. b) Brunner, H. Synthesis 1988, 645-654.
17. c) Ojima, I.; Clos, N.; Bastos, C. Tetrahedron 1989, 45, 6901-6939.
18. d) Noyori, R. Chem. Soc. Rev. 1989, 18, 187-208.
19. e) Brown, J. M.; Davies, S. G. Nature 1989, 342, 631-636.
20. f) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
21. g) Catalytic Asymmetric Synthesis, Tetrahedron: Asymmetry (Special Issue); Brown, J. M., Ed., 1991, 2, 481-732.
22. h) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
23. i) Catalytic Asymmetric Synthesis Ojima, I., Ed., VCH, Weinheim, 1993.
24. j) Noyori, R. Asymmetric Catalysis in Organic Synthesis Wiley, New York, 1994.
25. k) Bolm, C. in Advanced Asymmetric Synthesis Stephenson, G. R., Ed., Blackie Academic and Professional, New York, 1996, pp. 9-26.
26. l) Kagan, H. B.; Girard, C.; Guillaneux, D.; Rainford, D.; Samuel, O.; Zhang, S. Y.; Zhao, S. H. Acta Chem. Scand. 1996, 50, 345-352.
27. Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.-I.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596-1597.
28. a) Rinaldi, P. L.; Naidu, M. S. R.; Conaway, W. E. J. Org. Chem. 1982, 47, 3987-3991.
29. b) Ref. 3, Chapter 13, pp. 1057-1059.
30. c) See also: Dagani, R. Chem. Eng. News 1996, Sept. 23, 17-18.
31. Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357.
32. Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439.
33. Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113-126.
34. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070.
35. For a discussion, see Ref. 3, Chapter 6, pp. 217-221.
36. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
37. Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.
38. Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
39. For an excellent criticism: Noyori, R. Chem. Eng. News 1997, March 31, 4.
40. Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
41. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. J. Chem. Soc., Chem. Commun. 1993, 182-183.
42. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191-1203.
43. For a review on asymmetric ene reactions in organic synthesis: Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
44. Mikami, K.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1623-1624.
45. Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671-5680.
46. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255-265.
47. Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 833-834.
48. Tanaka, K.; Matsui, J.; Kawabata, Y.; Suzuki, H.; Watanabe, A. J. Chem. Soc., Chem. Commun. 1991, 1632-1634.
49. a) Rossiter, B. E.; Eguchi, M.; Hernández, A. E.; Vickers, D.; Medich, J.; Marr, J.; Heninis, D. Tetrahedron Lett. 1991, 32, 3973-3976.
50. b) For an excellent review on asymmetric conjugate additions: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806.
51. Rossiter, B. E.; Miao, G.; Swingle, N. M.; Eguchi, M.; Hernández, A. E.; Patterson, R. G. Tetrahedron: Asymmetry 1992, 3, 231-234.
52. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A.E.; Vickers, D.; Fluckinger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965-986.
53. Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1993, 153-157.
54. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467-4478.
55. a) Bolm, C. Tetrahedron: Asymmetry 1991, 2, 701-704.
56. b) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205-207.
57. De Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron 1994, 50, 4479-4491.
58. Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584.
59. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820.
60. Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1990, 1364-1365.
61. Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1992, 3135-3140.
62. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
63. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363-2364.
64. Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851-854.
65. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529-4533.
66. Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800-9801.
67. Alcock, N. W.; Brown, J. M.; Maddox, P. J. J. Chem. Soc., Chem. Commun. 1986, 1532-1533.
68. Brown, J. M.; Maddox, P. J. Chirality 1991, 3, 345-354.
69. Maruoka, K., Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 789-790.
70. Faller, J. W.; Parr, J. J. Am. Chem. Soc. 1993, 115, 804-805.
71. Faller, J. W.; Tokunaga, M. Tetrahedron Lett. 1993, 34, 7359-7362.
72. Mikami, K.; Matsukawa, S. Nature 1997, 385, 613-615.
73. For a brief survey: Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659.
74. a) Mason, S. F. Chemical Evolution: Origins of the Elements, Molecules, and Living Systems Clarendon Press, Oxford.
75. b) Wintner, E. A.; Conn, M. M.; Rebek, Jr., J. Acc. Chem. Res. 1994, 27, 198-203.
76. Frank, F. C. Biochim. Biophys. Acta 1953, 11, 459-463.
77. a) Wynberg, H. Chimia 1989, 43, 150-152.
78. b) See also: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
79. a) Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265-7266.
80. b) Alberts, A. H.; Wynberg, H. J. Chem. Soc., Chem. Commun. 1990, 453-454.
81. Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
82. Rautenstrauch, V.; Mégard, P.; Bourdin, B.; Furrer, A. J. Am. Chem. Soc. 1992, 114, 1418-1428.
83. a) Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740-6741.
84. b) Very recently it has also been demonstrated that the added cyanohydrin does not have to be the same as the product cyanohydrin. Thus in the conversion of cyclohexanecarboxaldehyde to its (S)-cyanohydrin, the addition of 8 mol% of (S)-benzaldehyde cyanohydrin raised the ee from 42% to 67%: Kogut, E. F.; Thoen, J. C.; Lipton, M. A. Abstract presented at the 213th ACS National Meeting in San Francisco; for a comment see Stinson, S. C. Chem. Eng. News 1997, April 28, 26-27.
85. b) Very recently it has also been demonstrated that the added cyanohydrin does not have to be the same as the product cyanohydrin. Thus in the conversion of cyclohexanecarboxaldehyde to its (S)-cyanohydrin, the addition of 8 mol% of (S)-benzaldehyde cyanohydrin raised the ee from 42% to 67%: Kogut, E. F.; Thoen, J. C.; Lipton, M. A. Abstract presented at the 213th ACS National Meeting in San Francisco; for a comment see Stinson, S. C. Chem. Eng. News 1997, April 28, 26-27.
86. Shvo, Y.; Gal, M.; Becker, Y.; Elgavi, A. Tetrahedron: Asymmetry 1996, 7, 911-924.
87. Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982-983.
88. Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789-792.
89. Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637-638.
90. ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885-886.
91. Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767-768.
92. Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471-472.
93. Mikami, K.; Matsukawa, S.; Nagashima, M.; Funabashi, H.; Morishima, H. Tetrahedron Lett. 1997, 38, 579-582.
94. Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815-816.
95. Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783-8786.
96. Pauly, M. E.; Pringle, W. C.; Merlic, C. A. Abstract presented at the 213th ACS National Meeting in San Francisco, CA, April 13-17, 1997; Abstracts Book, #479.