Chiral Lewis acid catalyzed ene-reactions

Current Organic Chemistry

Volumn 4, Issue 3, 2000, Pages 305-342

  Dias, Luiz Carlos ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL COMPOUNDS;

ALUMINUM TITANIUMS; ALUMINUM-COPPER; CHIRAL LEWIS ACID; ENE REACTION; IMINE COMPOUNDS; LEWIS ACID CATALYSTS; RECENT PROGRESS; SYNTHETIC APPLICATION; [CARBONYL;

CATALYSTS;

ACID; ALUMINUM; CARBONYL DERIVATIVE; COPPER; IMINE; TITANIUM; YTTERBIUM;

CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034076631     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272003376274     Document Type: Review

References (110)

1. For very interesting papers about chiral drugs, see: (a) Thall, E. J. Chem. Ed., 1996, 3 (6), 481. (b) Stinson, S.C. Chemical & Engineering News, 1994, 38.
2. For very interesting papers about chiral drugs, see: (a) Thall, E. J. Chem. Ed., 1996, 3 (6), 481. (b) Stinson, S.C. Chemical & Engineering News, 1994, 38.
3. For a very interesting review paper dealing with the requirements for using enantioselective catalysis in the synthesis of fine chemicals, see: Blaser, H.U.; Studer, M. Chirality, 1999, 11(5-6), 459.
4. For excellent books dealing with the principles of asymmetric synthesis, see: (a) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, New York, Chichester, Brishane, Toronto, Singapore, 1995. (b) Beller, M.; Bolm, C. Eds., Transition Metals for Fine Chemicals and Organic Synthesis, Wiley-lnterscience: Chichester, UK, 1998.
5. For excellent books dealing with the principles of asymmetric synthesis, see: (a) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, New York, Chichester, Brishane, Toronto, Singapore, 1995. (b) Beller, M.; Bolm, C. Eds., Transition Metals for Fine Chemicals and Organic Synthesis, Wiley-lnterscience: Chichester, UK, 1998.
6. For a review about chiral Lewis acid catalyzed Diels-Alder reactions, see: Dias, L.C. J. Braz. Chem. Soc., 1997, 8, 289.
7. (a) For a comprehensive review of catalyzed enantioselective aldol reactions, see: Nelson, S.G. Tetrahedron:Asymmetry, 1998, 9, 357.
8. (b) For a review about chiral Lewis acid promoted asymmetric aldol reaction using oxazaborolidinones, see: Kiyooka, S. Rev. Heteroatom Chem., 1997, 17, 245.
9. For an extensive review on selective reactions using allylic metals, see: Yamamoto, Y.; Asao, N. Chem. Rev., 1993, 93, 2207.
10. (a) For an excellent review on asymmetric synthesis with chiral Lewis acid catalysts, see: Ishihara, K.; Yamamoto, H. Cat. Tech., 1997, 51.
11. (b) For an excellent review on chiral Lewis acids In catalytic asymmetric reactions, see: Narasaka, K. Synthesis, 1991, 1.
12. (a) For a very interesting paper about enantiomeric impurities in chiral catalysts, auxiliaries and synthons used in enantioselective synthesis, see: Armstrong, D.W.; Lee, J.T.; Chang, L.W. Tetrahedron:Asymmetry, 1998, 9, 143.
13. (b) Review article about the use of chiral metal(salen) complexes in asymmetric catalysis: Sherrington, D.C. Chem. Soc. Rev., 1999, 25 (2), 85.
14. For an excellent review about stoichiometric asymmetric processes, see: Regan, A.C. J. Chem. Soc., Perkin Trans. 1, 1999, 357.
15. (a) For an excellent review about catalytic asymmetric process, see: Wills, M. J. Chem. Soc. Perkin Trans. 1, 1998, 18, 3101.
16. (b) enantioselective desymmetrization: Willis, M.C. J. Chem. Soc., Perkin Trans. 1, 1999, 1765.
17. (a) For a very interesting review on transition-metal-based Lewis acid catalysts, see: Bosnich, B. Aldrichimica Acta, 1998, 31, 76,
18. (b) For the first synthesis and structural characterization of an enantiomerically pure planar-chiral Lewis acid complex, see: Tweddell, J.; Hoic, D.A.; Fu, G.C. J. Org. Chem., 1997, 62, 8286.
19. (b) For a very interesting review that highlights the progress that has been made in the field of Lewis acid catalysis of carbon-carbon-bond forming reactions in aqueous solution, see: Engberts, J.B.F.N.; Feringa, B.L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays-Bas, 1996, 115, 457.
20. For a review dealing with recent developments in asymmetric catalysis using synthetic polymers with main chain chirality, see: Pu, L. Tetrahedron Asymmetry, 1998, 9, 1457.
21. For an excellent review article about catalytic enantioselective construction of molecules with quaternary carbon stereocenters, see: Corey, E.J.; Guzman-Perez, A. Angew. Chem., Int. Ed. Engl., 1998, 37, 388.
22. Recent review article about catalytic asymmetric addition reactions of carbonyls: Jorgensen, K.A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res., 1999, 32, 605.
23. (a) Treibs, W.; Schmidt, H. Ber. Dtsch. Chem. Ges., 1927, 60, 2335.
24. (b) Grignard, V.; Doeuvre, J.C.R. Acad. Sci., 1930, 190, 1164.
25. (c) Ikeda, T.; Wakatsuki, K. J. Chem. Soc. Jpn., 1936, 57, 425.
26. (a) Alder, K.; Pascher, F.; Schmilz, A. Ber. Dtsch. Chem. Ges., 1943, 76, 27.
27. (b) Nobel Lectures-Chemistry, 1942-1962; Elsevier: Amsterdam, pp. 253-305, 1964.
28. (a) Klimova, E.I.; Arbuzov, Y.A. Dokl. Akad. Nauk. SSSR, 1965, 167, 419.
29. (b) Klimova, E.I.; Arbuzov, Y.A. Dokl. Akad. Nauk. SSSR, 1967, 173, 1332.
30. (c) Klimova, E.I.; Arbuzov, Y.A. J. Org. Chem. USSR Engl., 1968, 4, 1726.
31. Achmatowicz, J.O.; Szechner, B. J. Org. Chem., 1972, 37, 964.
32. Snider, B.B.; Straten, J.W.V. J. Org. Chem., 1979, 44, 3567.
33. Snider, B.B. Acc. Chem. Res., 1980, 13, 426.
34. Whitesell, J.K.; Chen, H.-H.; Lawrence, R.M. J. Org. Chem., 1985, 50, 4663.
35. Whitesell, J.K.; Lawrence, R.M; Chen, H.-H. J. Org. Chem., 1986, 51, 4779.
36. For mechanistic aspects of the ene-reaction, see: Paderes, G.D.; Jorgensen, W.L. J. Org. Chem., 1992, 57, 1904.
37. For a paper about the mechanism of the carbonyl-ene reaction, see; Achmatowicz, O.; Florjanczyk, E.B. Tetrahedron, 1996, 52, 8827.
38. For excellent reviews about asymmetric ene-reactions in organic synthesis, see: (a) Mikami, K.; Shimizu, M. Chem. Rev., 1992, 92, 1021. (b) Borzilleri, R.M.; Weinreb, S.M. Synthesis, 1995, 347. (c) Mikami, K. Pure & Appl. Chem., 1996, 68, 639. For reviews about general aspects of asymmetric carbonyl-ene-reactions, see: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett, 1992, 255. (b) Mikami, K. Advances In Asymmetric Synthes/s, Vol. 1, pp. 1-44, JAI Press, Inc., 1995.
39. For excellent reviews about asymmetric ene-reactions in organic synthesis, see: (a) Mikami, K.; Shimizu, M. Chem. Rev., 1992, 92, 1021. (b) Borzilleri, R.M.; Weinreb, S.M. Synthesis, 1995, 347. (c) Mikami, K. Pure & Appl. Chem., 1996, 68, 639. For reviews about general aspects of asymmetric carbonyl-ene-reactions, see: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett, 1992, 255. (b) Mikami, K. Advances In Asymmetric Synthes/s, Vol. 1, pp. 1-44, JAI Press, Inc., 1995.
40. For excellent reviews about asymmetric ene-reactions in organic synthesis, see: (a) Mikami, K.; Shimizu, M. Chem. Rev., 1992, 92, 1021. (b) Borzilleri, R.M.; Weinreb, S.M. Synthesis, 1995, 347. (c) Mikami, K. Pure & Appl. Chem., 1996, 68, 639. For reviews about general aspects of asymmetric carbonyl-ene-reactions, see: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett, 1992, 255. (b) Mikami, K. Advances In Asymmetric Synthes/s, Vol. 1, pp. 1-44, JAI Press, Inc., 1995.
41. For excellent reviews about asymmetric ene-reactions in organic synthesis, see: (a) Mikami, K.; Shimizu, M. Chem. Rev., 1992, 92, 1021. (b) Borzilleri, R.M.; Weinreb, S.M. Synthesis, 1995, 347. (c) Mikami, K. Pure & Appl. Chem., 1996, 68, 639. For reviews about general aspects of asymmetric carbonyl-ene-reactions, see: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett, 1992, 255. (b) Mikami, K. Advances In Asymmetric Synthes/s, Vol. 1, pp. 1-44, JAI Press, Inc., 1995.
42. For excellent reviews about asymmetric ene-reactions in organic synthesis, see: (a) Mikami, K.; Shimizu, M. Chem. Rev., 1992, 92, 1021. (b) Borzilleri, R.M.; Weinreb, S.M. Synthesis, 1995, 347. (c) Mikami, K. Pure & Appl. Chem., 1996, 68, 639. For reviews about general aspects of asymmetric carbonyl-ene-reactions, see: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett, 1992, 255. (b) Mikami, K. Advances In Asymmetric Synthes/s, Vol. 1, pp. 1-44, JAI Press, Inc., 1995.
43. For a short review on catalytic asymmetric carbonyl ene-reactions, see: Berrisford, D.J.; Bolm, C. Angew. Chem., Int. Ed. Engl., 1995, 34, 1717.
44. For mechanistic studies of the metallo-ene-reaction, see: Gomez-Benjoa, E.; Cuerva, J.M.; Echavarren, A.M.; Martorell, G. Angew. Chem., Int. Ed. Engl, 1997, 36, 767.
45. For a recent review about thermal and Lewis acid catalyzed intramolecular ene-reactions of allenylsilanes, see: Weinreb, S.M.; Smith, D.T.; Jin, J. Synthesis, 1998, 509.
46. In 1997, Jenner described the effect of high-pressure kinetics of Lewis acid catalyzed cycloaddition and ene-reactions: Jenner, G. New J. Chem., 1997, 21, 1085.
47. For solvent effects in asymmetric hetero Diels-Alder and ene-reactions, see: Johannsen, M.; Jorgensen, K.A. Tetrahedron, 1996, 52, 7321.
48. Excellent and comprehensive reviews of intramolecular ene-reactions: (a) Conia, J.M.; Perchec, P. Le Synthesis, 1975, 1. (b) Taber, D.F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer Verlag: Berlim, 1984.
49. Excellent and comprehensive reviews of intramolecular ene-reactions: (a) Conia, J.M.; Perchec, P. Le Synthesis, 1975, 1. (b) Taber, D.F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer Verlag: Berlim, 1984.
50. Whitesell, J.K.; Bhattacharya, A.; Aguilar, D.A; Henke, K. J. Chem. Soc. Chem. Commun., 1982, 989.
51. Whitesell, J.K. Acc. Chem. Res., 1985, 18, 280
52. Whitesell, J.K.; Bhattacharya, A.; Buchanan, C.M. Chen, H.H.; Deyo, D.; James, D.; Liu, C.-L.; Minton, M.A. Tetrahedron, 1986, 42, 2993.
53. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett., 1988, 29, 3967.
54. For intramolecular ene-reactions of unsaturated aldehydes catalyzed by a chiral Lewis acid, see: (a) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett., 1985, 26, 5535. (b) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron, 1986, 42, 2203. (c) another example of an intramolecular ene-reaction: Cossy, J.; Bouzide, A.; Pfau, M. J. Org. Chem., 1997, 62, 7106.
55. For intramolecular ene-reactions of unsaturated aldehydes catalyzed by a chiral Lewis acid, see: (a) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett., 1985, 26, 5535. (b) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron, 1986, 42, 2203. (c) another example of an intramolecular ene-reaction: Cossy, J.; Bouzide, A.; Pfau, M. J. Org. Chem., 1997, 62, 7106.
56. For intramolecular ene-reactions of unsaturated aldehydes catalyzed by a chiral Lewis acid, see: (a) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett., 1985, 26, 5535. (b) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron, 1986, 42, 2203. (c) another example of an intramolecular ene-reaction: Cossy, J.; Bouzide, A.; Pfau, M. J. Org. Chem., 1997, 62, 7106.
57. (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc., 1989, 111, 1940.
58. (b) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc., 1990, 112, 3949.
59. Terada, M.; Matsukawa, S.; Mikami, K. Chem. Commun., 1993, 327.
60. Mikami, K.; Terada, M.; Sawa, E.; Nakai, T. Tetrahedron Lett., 1991, 32, 6571.
61. In the ene-cyclizations, the carbon members where the tether connects the [1,5]-hydrogen shift system, are expressed in (m,n) fashion.
62. Mikami, K.; Sawa, E.; Terada, M. Tetahedron:Asymmetry, 1991, 2, 1403.
63. In 1990, Ziegler described an interesting synthesis of trichothecene anguidine, in which one of the steps was an asymmetric ene-reaction conducted in the presence of chiral catalysts to give relatively high diastereoselectivity but only low levels of enantioselectivity. Ziegler, F.E.; Sobolov, S.B. J. Am. Chem. Soc., 1990, 112, 2749.
64. Mikami, K.; Yajima, T.; Terada, M.; Uchimaru, T. Tetrahedron Lett., 1993, 34, 7591.
65. Terada, M.; Mikami, K. J. Chem. Soc., Chem. Commun., 1994, 833.
66. Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett., 1995, 36, 1861.
67. Mikami, K.; Motoyama, Y.; Terada, M. Inorganica Chimica Acta, 1994, 222, 71.
68. Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett., 1994, 35, 6693.
69. It should be noted that the chiral titanium complexes derived from binaphthol ditrifylamine (R)-49 afforded very low levels of asymmetric induction (only 3% ee).
70. Mikami, K.; Matsukawa, S. Tetrahedron Lett., 1994, 35, 3133,
71. Mikami, K.; Yoshida, A. Synlett, 1995, 29.
72. Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc., 1992, 114, 9242.
73. (a) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett., 1996, 37, 8515.
74. (b) see also: Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl., 1997, 36, 858.
75. Faller, J.W.; Liu, X. Tetrahedron Lett., 1996, 37, 3449.
76. Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett., 1998, 39, 3359.
77. A very similar approach for the synthesis of A ring has been used by Courtney and coworkers: Courtney, L.F.; Lange, M.; Uskokovié, M.R.; Noukulich, P.M. Tetrahedron Lett., 1998, 39, 3363.
78. (a) Mikami, K.; Matsukawa, S. J. Am.Chem. Soc., 1993, 115, 7039.
79. (b) Shoda, H.; Nakamura, T.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1993, 34, 6281.
80. (a) Mikami, K.; Matsukawa, S. Nature, 1997, 385, 613.
81. (b) Review on chiral llgand acceleration: Berrisford, D.J.; Bolm, C.; Sharpless, K.B. Angew. Chem., Int. Ed. Engl., 1995, 34, 1059.
82. Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew, Chem., Int Ed. Engl., 1997, 36, 2768.
83. Chavarot, M.; Byrne, J.J.; Chavant, P.Y.; Pardillos-Guindet, J.; Vallée, Y. Tetrahedron:Asymmetry, 1998, 9, 3889.
84. Mikami, K.; Matsukawa, S.; Sawa, E.; Harada, A.; Koga, N. Tetrahedron Lett., 1997, 38, 1951.
85. (a) Dyer, A. An Introduction to Zeolite Molecular Sieves, Wiley, Chichester, 1988.
86. (b) Davis, M.E. Acc. Chem. Res., 1993, 26, 111.
87. Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun., 1997, 281.
88. (a) Terada, M.; Mikami, K.; Nakal, T. J. Chem. Soc., Chem. Commun., 1990, 1623.
89. (b) Mikami, K.; Terada, M. Tetrahedron, 1992, 43, 5671.
90. Corey, E.J.; Rohde, J.J.; Fisher, A.; Azimioara, M.D. Tetrahedron Lett., 1997, 38, 33.
91. (b) Corey, E.J.; Rohde, J.J. Tetrahedron Lett., 1997, 38, 37.
92. (c) Corey, E.J.; Barnes-Seeman, D.; Lee, T.W. Tetrahedron Lett., 1997, 38, 1699.
93. Corey, E.J.; Barnes-Seeman, D.; Lee, T.W.; Goodman, S.N. Tetrahedron Lett., 1997, 38, 6513.
94. Qian, C.; Huang, T. Tetrahedron Lett., 1997, 38, 6721.
95. (a) For a discussion on the coordination chemistry of Cu(II), see: Hathaway, B.J. In Comprehensive Coordination Chemistry, Wilkinson, G.; Gillard, R.D.; MaClevarty, J.A.; Eds.; Pergamon Press: Oxford, Vol. 5, pp. 533, 1989.
96. 2+: Otto, S.; Bertoncin, F.; Engberts, J.B.F.N. J. Am. Chem. Soc., 1996, 118, 7702.
97. 2-symmetric semicorrin and related ligands, see: Pfaltz, A. Synlett, 1999, 835.
98. 2-symmetric chiral bis(oxazoline)-copper complexes, see: Evans, D.A.; Peterson, G.S.; Johnson, J.S.; Barnes, D.M.; Campos, K.R.; Woerpel, K.A. J. Org. Chem., 1998, 63, 4541.
99. (b) For an excellent review about the use of C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis, see: Ghosh, A.K.; Mathiavanen, P.; Cappiello, J. Tetrahedron:Asymmetry, 1998, 9, 1
100. Johannsen, M.; Jorgensen, K.A. J. Org. Chem., 1995, 60, 5757.
101. Terada, M.; Mikami, K.; Takai, T. Tetrahedron Lett., 1991, 32, 935.
102. Gao, Y.; Lane-Bell, P.; Vederas, J.C. J. Org. Chem., 1998, 63, 2133.
103. (a) Evans, D.A.; Burgey, C.S.; Paras, N.A.; Vojkovsky, T.; Tregay, S.W. J. Am. Chem. Soc., 1998, 120, 5824.
104. (b) In a recent paper, Kanemasa and coworkers described the preparation and use of transition-metal aqua complexes of 4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline). The cationic aqua complexes prepared from their enantiopure ligand and various transition-metal (II) perchlorates are effective catalysts for the Diels-Alder reaction with excellent enantioselectivity and extreme chiral amplification, and high tolerance to water, alcohols, amines, and acids: Kanemasa, S.; Oderaotoshi, Y.; Sakaguchl, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D.P. J. Am. Chem. Soc., 1998, 120, 3074.
105. Evans, D.A.; Johnson, J.S.; Burgey, C.S.; Campos, K.R. Tetrahedron Lett., 1999, 40, 2879.
106. Yao, S.; Fang, X.; Jorgensen, K.A. Chem. Commun., 1998, 2547.
107. In this same paper, the authors have observed that the use of bis-(oxazollnes) and different Lewis acids leads only to moderate ee's.
108. Drury, W.J., III.; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc., 1998, 120, 11006.
109. Elder, A.M.; Rich, D.H. Org. Lett., 1999, 1(9), 1443.
110. For a very exciting review paper about nonlinear effects in asymmetric synthesis, see: Girard, C.; Kagan, H.B. Angew. Chem., Int. Ed. Engl., 1998, 37, 2922.