On the Ti-TADDOLate-Catalyzed Diels-Alder Addition of 3-Butenoyl-l,3-oxazolidin-2-one to Cyclopentadiene. General Features of Ti-BINOLate- and Ti-TADDOLate-Mediated Reactions

Journal of Organic Chemistry

Volumn 60, Issue 6, 1995, Pages 1788-1799

  Seebach, Dieter ^a   Dahinden, Robert ^a   Marti, Roger E ^a   Beck, Albert K ^a   Plattner, Dietmar A ^a   Kühnle, Florian N M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000826366     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00111a042     Document Type: Article

References (140)

1. Diplomarbeit (Master's Thesis) of R.E.M., ETH Zurich, 1992.
2. Part of the dissertation No. 10283 of D.A.P., ETH Zurich, 1993.
3. Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett. 1986, 1109-1112.
4. Seebach, D.; Beck, A. K.; Imwinkelried, R.; Roggo, S.; Wonnacott, A. Helv. Chim. Acta 1987, 70, 954-974.
5. This was observed previously for Ti-TADDOLate-mediated nu-cleophilic additions; see references cited in: Seebach, D.; Beck, A. K.; Schiess, M.; Widler, L.; Wonnacott, A. Pure Appl. Chem. 1983, 55, 1807-1822.
6. For a review article with references to the original literature see: Dahinden, R.; Beck, A. K.; Seebach, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester (expected publication date in early 1995; a copy of the manuscript may be requested from the corresponding author of the present paper).
7. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345.
8. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods; Scheffold, R., Ed.; Salle + Sauerlánder: Aarau (Switzerland) and Wiley: New York, 1983; Vol. 3, p 217.
9. Beck, A. K.; Bastani, B.; Plattner, D. A.; Fetter, W.; Seebach, D.; Braunschweiger, H.; Gysi, P.; LaVeccia, L. Chimia 1991, 45, 238-244.
10. Posner, G. H.; Carry, J.-C.; Lee, J. K.; Bull, D. S.; Dai, H. Tetrahedron Lett. 1994, 35, 1321-1324.
11. Posner, G. H.; Eydoux, F.; Lee, J. K.; Bull, D. S. Tetrahedron Lett. 7541-7544.
12. Posner, G. H.; Ishihara, Y. Tetrahedron Lett. 7545-7548.
13. Toda, F.; Tanaka, K. Tetrahedron Lett. 1988, 29, 551-554.
14. Toda, F.; Sato, A.; Tanaka, K.; Mak, T. C. W. Chem. Lett. 1989, 873-876.
15. Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
16. Nassimbeni, L. R.; Niven, M. L.; Tanaka, K.; Toda, F. J. Cryst. Spectrosc. 1991, 21, 451-457.
17. Toda, F.; Sato, A.; Nassimbeni, L. R.; Niven, M. L. J. Chem. Soc, Perkin Trans. 2 1991, 1971-1975.
18. Toda, F.; Tanaka, K.; Marks, D.; Goldberg, I. J. Org. Chem. 1991, 56, 7332-7335.
19. Weber, E.; Dorpinghaus, N.; Goldberg, I. J. Chem. Soc., Chem. Commun. 1988, 1566-1568.
20. Goldberg, I.; Stein, Z.; Weber, E.; Dorpinghaus, N.; Franken, S. J. Chem. Soc, Perkin Trans. 2 1990, 953-963.
21. Weber, E.; Dorpinghaus, N.; Wimmer, C.; Stein, Z.; Krupitsky, H.; Goldberg, I. J. Org. Chem. 1992, 57, 6825-6833.
22. Quinkert, G.; Del Grosso, M.; Bucher, A.; Bauch, M.; Doring, W.; Bats, J. W.; Dürner, G. Tetrahedron Lett. 1992, 33, 3617-3620.
23. Quinkert, G.; Becker, H.; Del Grosso, M.; Dambacher, G.; Bats, J. W.; Dürner, G. Tetrahedron Lett. 1993, 34, 6885-6888.
24. Quinkert, G.; Del Grosso, M. In Stereoselective Synthesis; Ottow, E., Schollkopf, K., Schulz, B.-G., Eds.; Springer: Berlin, 1993; pp 109-134.
25. Doring, W. Totalsynthese von (-)-Norgestrel über enantioselektive Diels-Alder-Reaktion. Dissertation, Fachbereich Chemie, Universitát Frankfurt/Main, Germany, 1994. In this thesis it is also shown that the titanate of (P)-BINOLate gives the same enantiomer preferentially which is formed with Ti-(S, S)-TADDOLate.
26. Cativiela, C.; López, P.; Mayoral, J. A. Tetrahedron Asymm. 1991, 2, 1295-1304.
27. Hafner, A.; Duthaler, R. O.; Marti, R.; Rhis, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321-2336.
28. Seebach, D.; Rheiner, P. B.; Beck, A. K.; Ktthnle, F. N. M.; Jaun, B. Pol. J. Chem. 1994, 68, 2397-2413.
29. Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289-6292.
30. Engler, T. A.; Letavic, M. A.; Reddy, J. P. J. Am. Chem. Soc. 1991, 113, 5068-5070.
31. Engler, T. A.; Letavic, M. A.; Takusagawa, F. Tetrahedron Lett. 1992, 33, 6731-6734.
32. Engler, T. A.; Letavic, M. A.; Lynch, K. O., Jr.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179-1183.
33. Von dem Bussche-Hiinnefeld, C.; Beck, A. K.; Lengweiler, U.; Seebach, D. Helv. Chim. Acta 1992, 75, 438-441.
34. Irurre, J.; Alonso-Alija, C.; Piniella, J. F.; Alvarez-Larena, A. Tetrahedron Asymm. 1992, 3, 1591-1596.
35. Seebach, D.; Plattner, D. A.; Beck, A. K.; Wang, Y. M.; Hunziker, D.; Fetter, W. Helv. Chim. Acta 1992, 75, 2171-2209.
36. Nakayama, K.; Rainier, J. D. Tetrahedron 1990, 46, 4165-4170.
37. Ichikawa, Y.-I.; Narita, A.; Shiozawa, A.; Hayashi, Y.; Narasaka, K. J. Chem. Soc, Chem. Commun. 1989, 1919-1921.
38. Narasaka, K.; Tanaka, H.; Kanai, F. Bull. Chem. Soc. Jpn. 1991, 64, 387-391.
39. Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743-5754.
40. Ito, Y. N.; Ariza, X.; Beck, A. K.; Bohác, A.; Canter, C.; Gawley, R. E.; Kühnle, F. N. M.; Tuleja, J.; Wang, Y. M.; Seebach, D. Helv. Chim. Acta 1994, 77, 2071-2110.
41. Dreisbach, C.; Kragl, U.; Wandrey, C. Synthesis 1994, 911-912.
42. Rothe-Streit, P. Stereoselektive Reaktionen mit definierten Titan-Komplexen. Neue chirale Chelatkomplexe mit l,4-Diol-l,4-Aminoalkohol-Liganden. Dissertation, Universitat Basel, Switzerland, 1994.
43. Guseinov, M. M.; Mamedov, E. G. Azerb. Khim. Zh. 1976, 46-48.
44. Hashimoto, S.-I.; Komeshima, N.; Koga, K. J. Chem. Soc, Chem. Commun. 1979, 437-438.
45. Takemura, H.; Komeshima, N.; Takahashi, I.; Hashimoto, S.-I.; Ikota, N.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1987, 28, 5687-5690.
46. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
47. Taschner, M. J. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press, Inc.: London, 1989; Vol. 1; pp 2-101.
48. Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129-158.
49. Waldmann, H. Synthesis 1994, 535-551.
50. Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290-8292.
51. Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979-3982.
52. Corey, E. J.; Roper, T. D.; Ishihara, K.; Sarakinos, G. Tetrahedron Lett. 1993, 34, 8399-8402.
53. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
54. Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
55. Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538.
56. Devine, P. N.; Oh, T. J. Org. Chem. 1992, 57, 396-399.
57. Bao, J.; Wulff, W. D. J. Am. Chem. Soc. 1993, 115, 3814-3815.
58. Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938-2939.
59. Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412-10413.
60. For review articles about the use of Ti-TADDOLates as chiral Lewis acids see ref 7. and: Narasaka, K. Synthesis 1991, 1-11.
61. Narasaka, K. In Organic Synthesis in Japan: Past, Present, and Future, Noyori, R., Ed.; Tokyo Kagaku Dozin: Tokyo, 1992; pp 283-290.
62. Narasaka, K.; Iwasawa, N. In Organic Synthesis: Theory and Applications, Hudlicky, T., Ed.; JAI Press Inc.: London, 1993; Vol. 2; pp 93-112.
63. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832.
64. Duthaler, R. O.; Hafner, A.; Alsters, P. L.; Bold, G.; Rihs, G.; Rothe-Streit, P.; Wyss, B. Inorg. Chim. Acta 1994, 222, 95-113.
65. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
66. Kaupp, G. Angew. Chem. 1994, 106, 768-770;
67. Angew. Chem., Int. Ed. Engl. 1994, 33, 728-729.
68. Toda, F.; Tanaka, K.; Ootani, M.; Hayashi, A.; Miyahara, I.; Hirotsu, K. J. Chem. Soc, Chem. Commun. 1993, 1413-1415.
69. Tsai, W.-L.; Hermann, K.; Hug, E.; Rohde, B.; Dreiding, A. S. Helv. Chim. Acta 1985, 68, 2238-2243.
70. Diter, P.; Taudien, S.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1994, 59, 370-373 and references cited therein.
71. Narasaka, K.; Inoue, M.; Yamada, T. Chem. Lett. 1986, 1967-1968.
72. The effect of high pressure on Ti-TADDOLate-mediated reactions was also studied: Tietze, L. F.; Ott, C.; Gerke, K.; Buback, M. Angew. Chem. 1993, 105, 1536-1538;
73. Angew. Chem., Int. Ed. Engl. 1993, 32, 1485-1486.
74. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954.
75. According to Narasaka et al. the alcohol is a “bystander” and does not react with A* (X = Y = Cl) to give the “real” catalyst: Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581-1584.
76. Schmidt, B.; Seebach, D. Angew. Chem. 1991, 103, 100-101;
77. Angew. Chem., Int. Ed. Engl. 1991, 30, 99-101.
78. Schmidt, B.; Seebach, D. Angew. Chem. 1991, 103, 1383-1385;
79. Angew. Chem., Int. Ed. Engl. 1991, 30, 1321-1323.
80. Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem. 1991, 103, 991-992;
81. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008-1009.
82. von dem Bussche-Hiinnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719-5730.
83. Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384.
84. Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922-1925.
85. Corey, E. J.; Houpis, I. N. Tetrahedron Lett. 1993, 34, 2421-2424.
86. Chapuis, C.; Jurczak, J. Helv. Chim. Acta 1987, 70, 436-440.
87. For other examples of nonlinear plots between NNNNc/< NNNNee of auxiliary and of product see: (a) Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agamí, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357.
88. Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34-55;
89. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
90. Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671-5680.
91. Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439.
92. Seebach, D. Angew. Chem. 1988, 100, 1685-1715;
93. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
94. Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradon, B.; Hidber, P. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammatter, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, B.; Stucky, G.; Fetter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitles, C.; Molins, E. Helv. Chim. Acta 1992, 75, 913-934.
95. Sakaki, J.-I.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1993, 76, 2654-2665.
96. Seebach, D.; Hayakawa, M.; Sakaki, J.-I.; Schweizer, W. B. Tetrahedron 1993, 49, 1711-1724.
97. Dobler, M. MacMoMo III–Molecular Modeling Program Version 1.1, Laboratory of Organic Chemistry, ETH Zürich, 1993.
98. Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673-3682.
99. Iwasawa, N.; Sugimori, J.; Kawase, Y.; Narasaka, K. Chem. Lett. 1989, 1947-1950.
100. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820.
101. Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693-6696.
102. Hayashi, Y.; Narasaka, K. Chem. Lett. 1990, 1295-1298.
103. Narasaka, K.; Hayashi, Y.; Shimada, S. Chem. Lett. 1988, 1609-1612.
104. Cahn, R. S.; Ingold, C. K.; Prelog, V. Experientia 1956, 12, 81-94.
105. Prelog, V.; Helmchen, G. Angew. Chem. 1982, 94, 614-631;
106. Angew. Chem., Int. Ed. Engl. 1982, 21, 567-583.
107. Seebach, D.; Prelog, V. Angew. Chem. 1982, 94, 696-702;
108. Angew. Chem. Int. Ed. Engl. 1982, 21, 654-660.
109. Narasaka, K.; Kanai, F.; Okudo, M.; Miyoshi, N. Chem. Lett. 1989, 1187-1190.
110. Cheest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
111. Chérest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205-2208.
112. Anh, N. T. Topics Curr. Chem. 1980, 88, 145.
113. Bürgi, H.-B.; Dunitz, J. D. Ace. Chem. Res. 1983, 16, 153-161.
114. Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117.
115. tl ca. 17.
116. To account for a second chiral ligand in the coordination sphere of the active center we could have a dimeric complex possibly formed through attachment at the position X in I-M. See also the recent report of an oxygen bridged dimeric complex formed upon heating in toluene a BINOLate TiCVi-PrOH mixture, with no consequence for the topicity of the catalyzed ene reaction: Terada, M.; Mikami, K. J. Chem. Soc, Chem. Commun. 1994, 833-834.
117. For NMR investigations of complexes formed from a BOX derivative and Sn or A1 Lewis acids see: Castellino, S. J. Org. Chem. 1990, 55, 5197-5200.
118. Castellino, S.; Dwight, W. J. J. Am. Chem. Soc. 1993, 115, 2986-2987.
119. For examples of reactions of BINOLates and TADDOLates with other metal centers such as boron (a), magnesium (b), aluminum (c), zirconium (d), molybdenum (e), and the lanthanides (f) see: Reference 32. Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561-1562.
120. Weber, B.; Seebach, D. Angew. Chem. 1992, 104, 96-97;
121. Angew. Chem., Int. Ed. Engl. 1992, 31, 84-86.
122. Angew. Chem., Int. Ed. Engl. Tetrahedron 1994, 50, 6117-6128; 7473-7484.
123. References 18 and 32. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6716.
124. Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
125. Singh, V. K. Synthesis 1992, 605-617. Dahinden, R. Diplomarbeit (Master's Thesis), ETH Zürich, 1991/92, unpublished results, (d) Reference 34d.
126. McConville, D. H.; Wolf, J. R.; Schrock, R. R. J. Am. Chem. Soc. 1993, 115, 4413-4414.
127. Reference 32c. Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
128. Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084.
129. Kobayashi, S.; Araki, M.; Hachiya, I. J. Org. Chem. 1994, 59, 3758-3759.
130. Sasai, H.; Kim, W.-S.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1994, 35, 6123-6126.
131. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 6325-6328.
132. Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636.
133. Marko, I. E.; Evans, G. R.; Declercq, J.-P. Tetrahedron 4557-4574.
134. In the reaction of quiñones with styrenes furnishing [2 + 2] cycloadducts 62, Engler and his collegues also observe the formation of [5 + 2] cycloadducts (bicyclo[3.2.1]oct-3-ene-2,8-diones) which have a configuration compatible with attack of the styrene to the 3- and 5-position of the quinone from the same face from which the [2 + 2] cycloaddition occuss (see K in Chart 5), see ref 22a. and: (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587.
135. Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 6588-6599.
136. Evans, D. A.; Chapman, K. T.; Bisaba, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
137. Ray, F. E.; Albertson, C. E. J. Am. Chem. Soc. 1948, 70, 1954-1955.
138. Schlenk, W.; Bergmann, E. Annal. Chem. Pharm. 1928, 463, 188-217.
139. Lorette, N. B.; Howard, W. L. J. Org. Chem. 1960, 25, 521-525.
140. Konig, W. A.; Lutz, S.; Wenz, G.; von der Bey, E. J. High Resol. Chromatogr. Chromatogr. Commun. 1988, 11, 506-509.