A Simple and Highly Diastereoselective One-Pot Synthesis of Mannich-Bases

Synlett

Volumn 1997, Issue 8, 1997, Pages 974-976

  Arend, Michael ^a   Risch, Nikolaus ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001945513     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-946     Document Type: Article

References (28)

1. a) Tramontini, M.; Angiolini, L. Mannich Bases, Chemistry and Uses; CRC: Boca Raton, 1994.
2. (b) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791.
3. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
4. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
5. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
6. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
7. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
8. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
9. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
10. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
11. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
12. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
13. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
14. Reviews on modern variants of the Mannich reaction: (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. 1997, in press. (b) Kleinman, E. F. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 893. Recent examples: (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981. (d) Agami, C.; Bihan, D.; Puchot-Kadouri, C. Tetrahedron 1996, 52, 9079. (e) Saidi, M. R.; Heydari, A.; Ipaktschi, J. Chem.Ber. 1994, 127, 1761. (f) Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233. (g) Nolen, E. G.; Allocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem. 1989, 101, 1041; Angew. Chem. Int. Ed. Engl. 1989, 28, 1067. (j) Seebach, D.; Schiess, M.; Schweizer, W. B. Chimia 1985, 39, 272.
15. (a) Risch, N.; Arend, M. Angew. Chem. 1994, 106, 2531; Angew. Chem. Int. Ed. Engl. 1994, 33, 2422.
16. (a) Risch, N.; Arend, M. Angew. Chem. 1994, 106, 2531; Angew. Chem. Int. Ed. Engl. 1994, 33, 2422.
17. (b) Arend, M.; Risch, N. Angew. Chem. 1995, 107, 2861; Angew. Chem. Int. Ed. Engl. 1995, 34, 2639.
18. (b) Arend, M.; Risch, N. Angew. Chem. 1995, 107, 2861; Angew. Chem. Int. Ed. Engl. 1995, 34, 2639.
19. (c) Risch, N.; Arend, M. In Houben-Weyl, 4th ed., Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; p 1925.
20. Olah, G. A.; Narang, S. C. Tetrahedron 1982, 38, 2225.
21. Schroth, W.; Jahn, U.; Ströhl, D. Chem. Ber. 1994, 127, 2013.
22. Preparation of the enamines 4: (a) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207. (b) Ito, Y.; Sawamura, M.; Kominami, K.; Saegusa, T. Tetrahedron Lett. 1985, 26, 5303. (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49.
23. Preparation of the enamines 4: (a) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207. (b) Ito, Y.; Sawamura, M.; Kominami, K.; Saegusa, T. Tetrahedron Lett. 1985, 26, 5303. (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49.
24. Preparation of the enamines 4: (a) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207. (b) Ito, Y.; Sawamura, M.; Kominami, K.; Saegusa, T. Tetrahedron Lett. 1985, 26, 5303. (c) Carlson, R.; Nilsson, Å. Acta Chim Scand. B 1984, 38, 49.
25. 4. The solvent was finally removed in a rotary evaporator without heating.
26. Wittland, C.; Arend, M.; Risch, N. Synthesis 1996, 367.
27. Grumbach, H.-J.; Arend, M.; Risch, N. Synthesis 1996, 883.
28. Merla, B.; Arend, M.; Risch, N. Synlett 1997, 177.