Enantioselective mannich-type reactions using a novel chiral zirconium catalyst for the synthesis of optically active β-amino acid derivatives

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8180-8186

  Ishitani, Haruro ^a   Ueno, Masaharu ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BETA AMINO ACID; ETHER DERIVATIVE; LIGAND; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034734313     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001642p     Document Type: Article

References (73)

1. Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Chapter 2.3, Vol. 2, p 893.
2. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
3. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
4. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
5. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
6. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
7. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
8. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
9. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
10. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
11. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
12. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
13. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
14. Diastereoselective asymmetric Mannich-type reactions. For example: (a) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881. (b) Arend, M. Risch, N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2861. (c) Matsumura, Y. Tomita, T. Tetrahedron Lett. 1994, 35, 3737. (d) Page, P. C. B.; Allin, S. M.; Collington, E. W.; Carr, R. A. E. J. Org. Chem. 1993, 58, 6902. (e) Frauenrath, H.; Arenz, T.; Raabe, G.; Zorn, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 83. (f) Nolen, E. G.; Aliocco, A.; Broody, M.; Zuppa, A. Tetrahedron Lett. 1991, 32, 73. (g) Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215. (h) Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987. (i) Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1067. (j) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603. (k) Gennari, C.; Venturini, I.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227. (l) Broadley, K.; Davies, S. G. Tetrahedron Lett. 1984, 25, 1743. (m) Seebach, D.; Betschart, C.; Schiess, M. Helv. Chim. Acta 1984, 67, 1593.
15. For enantioselectve Mannich-type reactions using stoichiometric amounts of chiral sources: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 39, 5287. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981. See also: Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233.
16. For enantioselectve Mannich-type reactions using stoichiometric amounts of chiral sources: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 39, 5287. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981. See also: Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233.
17. For enantioselectve Mannich-type reactions using stoichiometric amounts of chiral sources: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 39, 5287. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981. See also: Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233.
18. For enantioselectve Mannich-type reactions using stoichiometric amounts of chiral sources: (a) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 39, 5287. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520. (c) Enders, D.; Ward, D.; Adam, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 981. See also: Risch, N.; Esser, A. Liebigs Ann. Chem. 1992, 233.
19. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
20. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
21. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
22. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
23. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
24. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
25. Quite recently, several catalytic enantioselective Mannich-type reactions have been reported: (a) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (d) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. (e) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (f) Yamada, K.-I.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1999, 38, 3504. (g) Kambara, T.; Tomioka, K. Chem. Pharm. Bull. 1999, 47, 720.
26. For review articles of this topic: (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto Y., Eds.; Springer: Heidelgerg, 1999. Vol. 3, p 998. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095. (c) Groger, H.; Vogel, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. (d) Nelson, S. G. Tetrahedron: Asym. 1998, 9, 357. (e) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
27. For review articles of this topic: (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto Y., Eds.; Springer: Heidelgerg, 1999. Vol. 3, p 998. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095. (c) Groger, H.; Vogel, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. (d) Nelson, S. G. Tetrahedron: Asym. 1998, 9, 357. (e) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
28. For review articles of this topic: (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto Y., Eds.; Springer: Heidelgerg, 1999. Vol. 3, p 998. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095. (c) Groger, H.; Vogel, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. (d) Nelson, S. G. Tetrahedron: Asym. 1998, 9, 357. (e) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
29. For review articles of this topic: (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto Y., Eds.; Springer: Heidelgerg, 1999. Vol. 3, p 998. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095. (c) Groger, H.; Vogel, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. (d) Nelson, S. G. Tetrahedron: Asym. 1998, 9, 357. (e) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
30. For review articles of this topic: (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto Y., Eds.; Springer: Heidelgerg, 1999. Vol. 3, p 998. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095. (c) Groger, H.; Vogel, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. (d) Nelson, S. G. Tetrahedron: Asym. 1998, 9, 357. (e) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
31. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
32. Rare earths are also promising candidates for the catalytic activation of aldimines. See: (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
33. Rare earths are also promising candidates for the catalytic activation of aldimines. See: (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
34. Different types of chiral zirconium catalysts that are effective in ring-opening reactions of epoxides, Diels-Alder reactions, and polymerization, etc., were reported: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262, and references therein.
35. Different types of chiral zirconium catalysts that are effective in ring- opening reactions of epoxides, Diels-Alder reactions, and polymerization, etc., were reported: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262, and references therein.
36. Different types of chiral zirconium catalysts that are effective in ring- opening reactions of epoxides, Diels-Alder reactions, and polymerization, etc., were reported: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262, and references therein.
37. (a) McCarty, C. G. The Chemistry of the Carbon-Nitrogen Double Bond, Patai, S., Ed.; John Wiley & Sons: New York, 1970; Chapter 9.
38. (b) Biørgo, J.; Boyd, D. R.; Watson, C. G.; Jennings, W. B. J. Chem. Soc., Perkin Trans. 2 1974, 757.
39. (a) Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33.
40. (b) Corey, E. J.; Rohde, J. J. Tetrahedron Lett. 1997, 38, 38.
41. (c) Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Lett. 1997, 38, 1699.
42. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357.
43. Catalytic enantioselective allylation of aldehydes using a zirconium/ BINOL (1/1) catalyst was reported: (a) Bedeshi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (b) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K. J. Chem. Soc., Chem. Commun. 1997, 763.
44. Catalytic enantioselective allylation of aldehydes using a zirconium/ BINOL (1/1) catalyst was reported: (a) Bedeshi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (b) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K. J. Chem. Soc., Chem. Commun. 1997, 763.
45. tBuOH.
46. About 20 additives were examined.
47. We expected the imidazole derivatives coordinated the zirconium to form a monomeric structure.
48. For the use of 6,6′-dibromo-1,1′-bi-2-naphthol, see: (a) Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693. (b) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388.
49. For the use of 6,6′-dibromo-1,1′-bi-2-naphthol, see: (a) Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693. (b) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388.
50. The same level of enantiomeric excess was obtained when the reaction was performed at -78 °C.
51. 4.
52. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
53. Kunz, H.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1068.
54. The same levels of reactivity and selectivity were observed when using the isolated catalyst. The reaction of 1c with 2a gave 3c quantitatively in 90% ee (Cf. Table 3, entry 3.).
55. See Supporting Information.
56. A direct pathway from 5a to 6 may be possible.
57. We assume that this flipping leads to two isomeric structures. See also: Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161.
58. 13C NMR spectra of the mixture were almost the same as those of Sa at both room temperature and -30 °C. We assume that coordination of NMI to the zirconium is stronger than that of the aldimine to the zirconium
59. For the structure of 6, another form where the imino phenol deprotonates and one of the BINOL ligands protonates may be possible.
60. For silyl crossover experiments in aldol reactions, see: (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (c) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (d) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
61. For silyl crossover experiments in aldol reactions, see: (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (c) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (d) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
62. For silyl crossover experiments in aldol reactions, see: (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (c) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (d) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
63. For silyl crossover experiments in aldol reactions, see: (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (c) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (d) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
64. (a) Colvin, E. W.; McGarry, D.; Nugent, M. J. Tetrahedron 1988, 44, 4157. A similar species is known to catalyze aldol reactions of silyl enol ethers with aldehydes.
65. (b) Kobayashi, S.; Mukaiyama, T. Chem. Lett. 1989, 297.
66. (c) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247. See also ref 27b.
67. Preliminary experiments suggested that the reaction proceeded via acyclic transition states. When 1c was treated with (Z)-1-ethyldimethylsiloxy-1-methoxy-1-propene in the presence of the zirconium catalyst (10 mol %) in dichloromethane at -78 °C, the desired anti adduct was predominantly obtained in good enantiomeric excess (syn/anti = 20/80, 78% ee (anti)). On the other hand, the same anti adduct was obtained preferentially (syn/anti = 16/84, 52% ee (anti) when (E)-1-ethyldimethylsiloxy-1-methoxy-1-propene was used under the same reaction conditions.
68. (a) Carr, G. E.; Chambers, R. D.; Holmes, T. F. J. Chem. Soc., Perkin Trans. 1, 1988, 921.
69. See also: (b) Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014.
70. (c) Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832.
71. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
72. Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
73. The NMR spectra are shown in Supporting Information.