The direct catalytic asymmetric three-component Mannich reaction [21]

Journal of the American Chemical Society

Volumn 122, Issue 38, 2000, Pages 9336-9337

  List, Benjamin ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; KETONE DERIVATIVE; MANNICH BASE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034721440     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001923x     Document Type: Letter

References (31)

1. Reviews: (a) Kleinnmann, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1. (b) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070.
2. Reviews: (a) Kleinnmann, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1. (b) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070.
3. (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc 1997, 119, 2060-2061.
4. (b) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154.
5. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432.
6. (d) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
7. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
8. (f) For the only method that utilizes unmodified ketones, see the following: Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310 and Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857-8867. This report describes asymmetric three-component Mannich reactions. However, yields (≤16%) and ee's (≤64%) were modest.
9. (f) For the only method that utilizes unmodified ketones, see the following: Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 307-310 and Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857-8867. This report describes asymmetric three-component Mannich reactions. However, yields (≤16%) and ee's (≤64%) were modest.
10. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
11. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693- 1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
12. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693- 1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
13. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693- 1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
14. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693- 1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
15. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693- 1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
16. For asymmetric Mannich reactions utilizing stoichiometric chiral controller, see, for example: (a) Kober, R.; Papadopoulus, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693- 1701 (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287-5290. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981-984. (e) Zarghi, A.; Naimi-Jamal, M. R.; Webb, S. A.; Balalaie, S.; Saidi, M. R.; lpaktschi, J. Eur. J. Org. Chem. 1998, 197-200. For diastereoselective Mannich reactions, se, for example: (f) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593-1597. (g) Risch, N.; Arend, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2422-2423.
17. Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1, 1965-1967.
18. Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 1998, 120, 2768-2779, and references therein.
19. (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
20. (b) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386-7387. Our studies are based on the landmark contributions by Wiechert and Hajos and their collegues: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
21. (b) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386- 7387. Our studies are based on the landmark contributions by Wiechert and Hajos and their collegues: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
22. (b) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386- 7387. Our studies are based on the landmark contributions by Wiechert and Hajos and their collegues: Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
23. We have screened various other catalytic proline derivatives. All of these gave lower yields and ee's. See Supporting Information.
24. The absolute configuration of β-amino ketone 6 has been determined by correlation (chiral-phase HPLC) with aldol 7: 6a (equation presented)
25. For example, see: Bravo, P.; Guidetti, M.; Viani, F.; Zanda, M.; Markovsky, A. L.; Sorochinsky, A. E.; Soloshonok, I. V.; Soloshonok, V. A. Tetrahedron 1998, 54, 12789-12806. (10) We investigated three different anilines in Mannich reactions with isovaleraldehyde in pure acetone: p-chloroaniline (56% yield, 84% ee), o-anisidine (43% yield, < 10% ee), and 2-aminophenol (51% yield, < 10% ee).
26. 2), dr = 2:1, ee = 84% (major diastereomer), ee = 23% (minor diastereomer), 50% combined yield from cyclohexanone. 3-Pentanone and 3-methyl-butan-2-one did not react under these conditions.
27. In all these reactions, we used the ketone component in excess. However, Mannich reactions in which all three components are used stoichiometrically have been reported. See ref 4.
28. Review: O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326-329.
29. Review: Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576.
30. For amine-catalyzed asymmetric Diels-Alder reactions see: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244. (b) Serebryakov, E. P.; Nigmatov, A. G.; Shcherbakov, M. A.; Struchkova, M. I. Russ. Chem. Bull. 1998, 47, 82-90.
31. For amine-catalyzed asymmetric Diels-Alder reactions see: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244. (b) Serebryakov, E. P.; Nigmatov, A. G.; Shcherbakov, M. A.; Struchkova, M. I. Russ. Chem. Bull. 1998, 47, 82-90.