Planar and central chiral [2.2]paracyclophanes as powerful catalysts for asymmetric 1,2-addition reactions

Synlett

Volumn , Issue 15, 2004, Pages 2647-2669

  Bräse, Stefan ^a   Dahmen, Stefan ^b   Höfener, Sebastian ^a   Lauterwasser, Frank ^a   Kreis, Michael ^a   Ziegert, Robert E ^c  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b CYNORA GMBH   (Germany)

^c UNIVERSITY OF BONN   (Germany)

Author keywords

Asymmetric catalysis; Ligands; Nucleophilic additions; Paracyclophanes; Zinc

Indexed keywords

ALDEHYDE; ALKYL GROUP; ALKYNYL GROUP; IMINE; LIGAND; PARACYCLOPHANE DERIVATIVE;

ADDITION REACTION; AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 10844250041     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-836029     Document Type: Article

References (132)

1. Knowles, W. S.; Sabacky, M. J. Chem. Soc., Chem. Commun. 1968, 1445.
2. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
3. Noyori, R. Science 1990, 248, 1194.
4. (a) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1996; Angew. Chem. 2002, 114, 2096. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008; Angew. Chem. 2002, 114, 2108. (c) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024; Angew. Chem. 2002, 114, 2126.
5. (a) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1996; Angew. Chem. 2002, 114, 2096. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008; Angew. Chem. 2002, 114, 2108. (c) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024; Angew. Chem. 2002, 114, 2126.
6. (a) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1996; Angew. Chem. 2002, 114, 2096. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008; Angew. Chem. 2002, 114, 2108. (c) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024; Angew. Chem. 2002, 114, 2126.
7. (a) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1996; Angew. Chem. 2002, 114, 2096. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008; Angew. Chem. 2002, 114, 2108. (c) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024; Angew. Chem. 2002, 114, 2126.
8. (a) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1996; Angew. Chem. 2002, 114, 2096. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008; Angew. Chem. 2002, 114, 2108. (c) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024; Angew. Chem. 2002, 114, 2126.
9. (a) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1996; Angew. Chem. 2002, 114, 2096. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008; Angew. Chem. 2002, 114, 2108. (c) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024; Angew. Chem. 2002, 114, 2126.
10. Stinson, S. C. Chem. Eng. News 2001, 79, 45.
11. (a) Reich, H. J.; Cram, D. J. J. Am. Chem. Soc. 1969, 91, 3527.
12. (b) Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691.
13. (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
14. (b) Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441.
15. (c) Rossen, K.; Pye, P. J.; Maliakal, A.; Volante, R. P. J. Org. Chem. 1997, 62, 6462.
16. Gibson, S.; Knight, J. D. Org. Biomol. Chem. 2003, 1, 1256.
17. Bräse, S.; Lauterwasser, F.; Ziegert, R. E. Adv. Synth. Catal 2003, 345, 869.
18. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
19. Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741.
20. (a) Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 91; Angew. Chem. 1994, 106, 106. (b) Antonov, D.; Belokon, Y. N.; Ikonnikov, N. S.; Orlova, S. A.; Pisaevsky, A. P.; Raevski, N. I.; Rozenberg, V. I.; Sergeeva, E. V.; Struchkov, Y. T.; Tararov, V. I.; Vorontsov, E. V. J. Chem. Soc., Perkin Trans. 1 1995, 1873.
21. (a) Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 91; Angew. Chem. 1994, 106, 106. (b) Antonov, D.; Belokon, Y. N.; Ikonnikov, N. S.; Orlova, S. A.; Pisaevsky, A. P.; Raevski, N. I.; Rozenberg, V. I.; Sergeeva, E. V.; Struchkov, Y. T.; Tararov, V. I.; Vorontsov, E. V. J. Chem. Soc., Perkin Trans. 1 1995, 1873.
22. (a) Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 91; Angew. Chem. 1994, 106, 106. (b) Antonov, D.; Belokon, Y. N.; Ikonnikov, N. S.; Orlova, S. A.; Pisaevsky, A. P.; Raevski, N. I.; Rozenberg, V. I.; Sergeeva, E. V.; Struchkov, Y. T.; Tararov, V. I.; Vorontsov, E. V. J. Chem. Soc., Perkin Trans. 1 1995, 1873.
23. Rozenberg, V.; Danilova, T.; Sergeeva, E.; Vorontsov, E.; Starikova, Z.; Lysenko, K.; Belokon, Y. Eur. J. Org. Chem. 2000, 3295.
24. (a) Pastor, S. D.; Togni, A. J. Am. Chem. Soc. 1989, 111, 2333.
25. (b) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
26. (c) Pastor, S. D.; Togni, A. Helv. Chim. Acta 1991, 74, 905.
27. (d) The term 'Chiral Cooperativity' was used by Pastor and Togni to describe positive interaction of different chiral moieties surpassing their mere addition. The case of diminishing was not investigated by the authors. Therefore they used 'not cooperative' in the case of a 'mismatched pair'.
28. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1; Angew. Chem. 1985, 97, 1.
29. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1; Angew. Chem. 1985, 97, 1.
30. (b) Heathcock, C. H.; White, C. T. J. Am. Chem. Soc. 1979, 101, 7076.
31. (c) Horeau, A.; Kagan, H.-B.; Vigneron, J.-P. Bull. Soc. Chim. Fr. 1968, 3795.
32. (a) Hayashi, T.; Tajika, M.; Tamao, K.; Kumada, M. J. Am. Chem. Soc. 1976, 98, 3718.
33. (b) Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
34. (a) Bolm, C.; Muniz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860.
35. (b) Bolm, C.; Muniz, K.; Hildebrand, J. P. Org. Lett. 1999, 1, 491.
36. For studies on chiral cooperatively in axial- and central-chiral ligands, see: (a) Buisman, G. J. H.; van der Veen, L. A.; Klootwijk, A.; de Lange, W. G. I.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Organometallics 1997, 16, 2929.
37. (b) Cserépi-Szucs, S.; Tóth, I.; Párkányi, L.; Bakos, J. Tetrahedron: Asymmetry 1998, 9, 3135.
38. (c) Cserépi-Szucs, S.; Huttner, G.; Zsolnai, L.; Szölosy, A.; Hegedüs, C.; Bakos, J. Inorg. Chim. Acta 1999, 296, 222.
39. (a) Hopf, H.; Barrett, D. G. Liebigs Ann. 1995, 449.
40. (b) Cipiciani, A.; Fringuelli, F.; Mancini, V.; Piermatti, O.; Pizzo, F.; Ruzziconi, R. J. Org. Chem. 1997, 62, 3744.
41. (c) Pamperin, D.; Schulz, C.; Hopf, H.; Syldatk, C.; Pietzsch, M. Eur. J. Org. Chem. 1998, 1441.
42. (d) Rozenberg, V.; Danilova, T.; Sergeeva, E.; Vorontsov, E.; Starikova, Z.; Korlyukov, A.; Hopf, H. Eur. J. Org. Chem. 2002, 468.
43. (a) Hoffmann, R. W.; Ditrich, K. Synthesis 1983, 107.
44. (b) Krohn, K.; Rieger, H.; Hopf, H.; Barrett, D.; Jones, P. G.; Doring, D. Chem. Ber. 1990, 123, 1729.
45. Dahmen, S.; Bräse, S. Tetrahedron: Asymmetry 2001, 12, 2845.
46. Sergeeva, E. V.; Rozenberg, V. I., Vorontsov, E. V.; Danilova, T. I.; Starikova, Z. A.; Yanovsky, A. I.; Belokon, Y. N.; Hopf, H. Tetrahedron: Asymmetry 1996, 7, 3445.
47. Kane, V. V.; Gerdes, A.; Grahn, W.; Ernst, L.; Dix, I.; Jones, P. G.; Hopf, H. Tetrahedron Lett. 2001, 42, 373.
48. (a) Cipiciani, A.; Fringuelli, F.; Mancini, V.; Piermatti, O.; Scappini, A. M.; Ruzziconi, R. Tetrahedron 1997, 53, 11853.
49. (b) Pamperin, D.; Schulz, C.; Hopf, H.; Syldatk, C.; Pietzsch, M. Eur. J. Org. Chem. 1998, 1441.
50. Kreis, M. unpublished results.
51. Still, I. W. J.; Natividad-Preyra, R.; Toste, F. D. Can. J. Chem. 1999, 77, 113.
52. Miranda, E. I.; Díaz, M. J.; Rosado, I.; Soderquist, J. A. Tetrahedron Lett. 1994, 50, 3221.
53. Wipf, P.; Kendall, C. Chem.-Eur. J. 2002, 8, 1778.
54. Danilova, T.; Rozenberg, V.; Vorontsov, E. V.; Starikova, Z.; Hopf, H. Tetrahedron: Asymmetry 2003, 14, 1375.
55. Danilova, T.; Rozenberg, V. I.; Sergeeva, E. V.; Starikova, Z. A.; Bräse, S. Tetrahedron: Asymmetry 2003, 14, 2013.
56. The transfer of the planar cylopentadienyl moiety of the ferrocene to benzenederivatives as done by Bolm et al. is risky, because of the change of the ortho-angle from 72° for the ferrocene to 60° for the benzenederivatives. These changes in the molecule geometry make it extremely difficult to derive the exact nature of the transition state from the one of the ferrocene.
57. To give the reader the opportunity to compare the results of the catalysis directly with the ligand structure, we do this without a detailed summary of the reactions. Further in this chapter, we will only show the catalyst and its results in the diethylzinc addition to benzaldehyde with the conditions as shown in Scheme 12.
58. Dahmen, S. PhD Thesis; RWTH Aachen, 2002.
59. Lauterwasser, F. unpublished results.
60. Energy minimization of the corresponding conformers were done with Chem3D Pro and CS MOPAC Pro.
61. In a PM3 calculation of the conformers done by J. Rudolph with the program Spartan 2001 (Wavefunction Inc., California) the results of the MNDO-analysis werde confirmed, resulting in conformer A as the conformer with the lowest energy. Although the differences in energy by this method are only 5 kcal/mol and therefore a bit lower as with MNDO, they are still high enough to make any consideration of the conformer B superfluous, (1 kcal = 4.1868 kJ).
62. The energy differences of the μ-O structures are only between 1-3 kcal/mol.
63. (a) Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998.
64. (b) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77.
65. Rasmussen, T.; Norrby, P.-O. J. Am. Chem. Soc. 2001, 123, 2464.
66. (a) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.
67. (b) Dahmen, S.; Lauterwasser, F.; Vanderheiden, S.; Bräse, S. unpublished.
68. (c) Wipf, P.; Pierce, J. G.; Wang, X. Tetrahedron: Asymmetry 2003, 14, 3605; and references cited therein.
69. Dahmen, S.; Bräse, S. Chem. Commun. 2002, 26.
70. Nugent, W. A. Org. Lett. 2002, 4, 2133.
71. Höfener, S.; Lauterwasser, F.; Bräse, S. Adv. Synth. Catal. 2004, 346, 755.
72. Dahmen, S.; Bräse, S. unpublished.
73. Allyl alcohols are substrates for, e.g., cyclopropanation reactions, aziridination reactions, ene-reactions, epoxidations. dihydroxylations, methoxy selenations, iodo hydroxylations, brominations, and allylic substitution reactions.
74. (a) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645.
75. (b) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777.
76. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
77. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
78. (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170.
79. (b) This reaction was recently extended to intramolecular cyclization reactions: Oppolzer, W.; Radinov, R. N.; El-Sayed, E. J. Org. Chem. 2001, 66, 4766.
80. The addition of vinylzinc has also been studied: (a) von dem Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719.
81. (b) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257.
82. (c) Shibata, T.; Nakatsui, K.; Soai, K. Inorg. Chim. Acta 1999, 296, 33.
83. (a) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
84. (b) Wipf, P.; Xu, W. Org. Synth. 1997, 74, 205.
85. (c) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
86. Dahmen, S.; Bräse, S. Org. Lett. 2001, 3, 4119.
87. Using these modifications, the aldehyde could be added in one portion, which is a significant practical improvement over the original Oppolzer protocol, where the aldehyde had to be added over a period of 20 min to obtain high enantioselectivities.
88. The absolute configuration was assigned by comparison of the optical rotation with the literature known compounds (S)-1-(4-chlorophenyl)hept-2-en-1- ol and (5)-1-phenylnon-2-en-1-ol, respectively, and the assumption of a unanimous reaction pathway for all other aldehyde substrates. The absolute configuration of the allyl alcohol products 51 is consistent with the induction observed in the diethylzinc addition to aldehydes with the ligands 5a and 6a.
89. (a) Nehl, H.; Scheldt, W. J. Organomet. Chem. 1985, 289, 1.
90. (b) Mynott, R.; Gabor, B.; Lehmkuhl, H.; Doering, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 335.
91. (a) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem. Int. Ed. 2000, 39, 3465; Angew. Chem. 2000, 112, 3607.
92. (a) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem. Int. Ed. 2000, 39, 3465; Angew. Chem. 2000, 112, 3607.
93. (b) Blacker, J. In Proceedings of the 3rd International Conference on the Scale Up of Chemical Processes; Laird, T., Ed.; Scientific Update: Mayfieldn/ East Sussex/Great Britain, 1998.
94. Alvaro, G.; Pacioni, P.; Savoia, D. Chem.-Eur. J. 1997, 3, 726.
95. Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH: Weinheim, 1995.
96. For a recent review, see: Pu, L. Tetrahedron 2003, 59, 9873.
97. Ishizaki, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 1901.
98. (a) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
99. (b) Boyall, D.; López, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233.
100. (c) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. N. Acc. Chem. Res. 2000, 33, 373.
101. (d) Anand, N. K.; Carreira, E. N. J. Am. Chem. Soc. 2001, 123, 9687.
102. 2Zn in hexane: 100 g (810 mmol) 80.90 $ (= 0.1 $/mmol). Prices taken from Acros Organics.
103. Xu, M.-H.; Pu, L. Org. Lett. 2002, 4, 4555.
104. Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850.
105. This behavior is untypical for mixed zinc species. The equilibrium could be influenced by the very low solubility of the dialkynylzinc reagents.
106. The clear supernant solution gives rise to the ethylation product in >80% yield.
107. For selected references in this field, see: (a) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem. Int. Ed. 2001, 40, 3284; Angew. Chem. 2001, 113, 3382.
108. For selected references in this field, see: (a) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem. Int. Ed. 2001, 40, 3284; Angew. Chem. 2001, 113, 3382.
109. (b) Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850.
110. (c) Rudolph, J.; Schmidt, F.; Bolm, C. Adv. Synth. Catal. 2004, 346, 867.
111. For selected APIs, see: (S)-Carbinoxamine: (a) Roszowski, A. P.; Govier, W. M. Pharmakologist 1959, 1, 60.
112. (b) Hunt, J. H. J. Chem. Soc. 1961, 2228.
113. (c) Barouh, V.; Dall, H.; Patel; D.; Kite, G. J. Med. Chem. 1971, 14, 834.
114. (d) James, M. N. G.; Williams, G. J. B. Can. J. Chem. 1974, 52, 1872.
115. (e) (R)-Neobenodin and (R)-orphenadrin
116. (f) Casy, A. F.; Drake, A. F.; Ganellin, C. R.; Mercer, A. D. Chirality 1992, 4, 356.
117. (g) van der Stelt, C.; Heus, W. J.; Nauta, W. T. Arzneim.-Forsch. 1969, 19, 2010.
118. (h) Rekker, R. F.; Timmerman, H.; Harms, A. F.; Nauta, W. T. Arzneim.-Forsch. 1971, 21, 688.
119. (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153.
120. (b) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 4837.
121. (c) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 5675.
122. (d) Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986; Angew. Chem. 1998, 110, 2092.
123. (d) Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986; Angew. Chem. 1998, 110, 2092.
124. (a) Okhuma, T.; Koizurni, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659.
125. (b) Noyori, R.; Okhuma, T. Pure Appl. Chem. 1999, 71, 1493.
126. Hermanns, N. PhD Thesis; RWTH: Aachen, 2002.
127. Rudolph, J. PhD Thesis; RWTH: Aachen, 2004.
128. (a) Dahmen, S.; Bräse, S. J. Am. Chem. Soc. 2002, 124, 5940.
129. (b) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem. Int. Ed. 2002, 41, 3692; Angew. Chem. 2002, 114, 3844.
130. (b) Hermanns, N.; Dahmen, S.; Bolm, C.; Bräse, S. Angew. Chem. Int. Ed. 2002, 41, 3692; Angew. Chem. 2002, 114, 3844.
131. Bräse, S.; Dahmen, S.; Vogt, H. to be submitted.
132. Knepper, K.; Ziegert, R. E.; Bräse, S. Tetrahedron 2004, 60, 8591.