Direct and highly enantioselective synthesis of ferrocenes with planar chirality by (-)-sparteine-mediated lithiation

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 685-686

  Tsukazaki, M ^a   Tinkl, M ^a   Roglans, A ^a   Chapell, B J ^a   Taylor, N J ^a   Snieckus, V ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000527506     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953246q     Document Type: Article

References (38)

1. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
2. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
3. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
4. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
5. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
6. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
7. Pioneering study: (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482. Recent work: (b) Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568. (c) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (d) Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. (f) Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
8. After the submission of this manuscript, a report appeared describing the asymmetric metalation of diphenylphosphinylferrocene with chiral lithium amide bases, resulting in moderate enantioinduction (55% ee): Price, D.; Simpkins, N. S. Tetrahedron Lett. 1995, 36, 6135.
9. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
10. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
11. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
12. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
13. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
14. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
15. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
16. Schlögl, K. Top. Stereochem. 1967, 1, 39. See, inter alia: Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593. For other methods to obtain ferrocenes with planar chirality, see: Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem. 1975, 91, 73. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4351. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061. David, D. M.; Kane-Maguire, L. A. P.; Pyne, S. G. J. Chem. Soc., Chem. Commun. 1990, 888.
17. Nicolosi, G.; Patti, A.; Morrone, R.; Piattelli, M. Tetrahedron: Asymmetry 1994, 5, 1275.
18. Snieckus, V. Chem. Rev. 1990, 90, 879.
19. (a) Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1944, 66, 1479.
20. (b) Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231 and references cited therein. For original observations:
21. (b) Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231 and references cited therein. For original observations:
22. (c) Aratani, T.; Gonda, T.; Nozaki, H. Tetrahedron Lett. 1969, 2265; Tetrahedron 1970, 26, 5453.
23. (c) Aratani, T.; Gonda, T.; Nozaki, H. Tetrahedron Lett. 1969, 2265; Tetrahedron 1970, 26, 5453.
24. (a) Togni, A., Hayashi, T., Eds. Ferrocenes: Homogeneous Catalysis. Organic Synthesis, Materials Science; VCH: Weinheim. 1995. Illustrative examples:
25. (b) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
26. (c) Nicolosi, G.; Patti, A.; Morrone, R.; Piattelli, M. Tetrahedron: Asymmetry 1994, 5, 1639.
27. (d) Lion-Dagan, M.; Marx-Tibbon, S.; Katz, E.; Willner, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 1604.
28. 2 in 74% yield after recrystallization (hexane).
29. For DoM chemistry of ferrocenes, see ref 1f.
30. 2O and t-BuOMe produced 94% and 97% yields and 74% and 67% ee. respectively.
31. CHIRALCEL OD, CHIRALCEL OK, and CHIRALCEL OJ chiral columns were used. For details, see supporting information.
32. w and GOF (for 5006 data with F > 6.0σ(F)) of 0.0283, 0.0298, and 1.59, respectively, for solution using the S model. The corresponding values for solution of the R model were 0.0430, 0.0467, and 2.49.
33. 1/2 = 60 h). This intriguing observation may be tentatively rationalized by substituted Cp-aryl ligand exchange. For similar examples, see: Slocum, D. W.; Tucker, S. P.; Engelmann, T. R. Tetrahedron Lett. 1970, 621. Roman, E.; Astruc, D.; des Abbayes, H. J. Organomet. Chem. 1981, 219, 211.
34. 1/2 = 60 h). This intriguing observation may be tentatively rationalized by substituted Cp-aryl ligand exchange. For similar examples, see: Slocum, D. W.; Tucker, S. P.; Engelmann, T. R. Tetrahedron Lett. 1970, 621. Roman, E.; Astruc, D.; des Abbayes, H. J. Organomet. Chem. 1981, 219, 211.
35. Related chiral ferrocenyl amino alcohols are very efficient catalysts for the enantioselective addition of diethylzinc to aldehydes: Butsugan, Y.; Araki, S.; Watanabe, M. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995; pp 143-169. See also ref 6c.
36. Similar behavior with parallel implications has been observed in deprotonations of the TMS derivative of a chiral ferrocenyloxazoline (ref 1f).
37. Quesnelle, C. A.; Familoni, O. B.; Snieckus, V. Synlett 1994, 349 and references cited therein.
38. Unoptimized yield. For similar dehalogenations observed during cross-coupling reactions, see: Nguyen, P.; Yuan, Z.; Agocs, L.; Lesley, G.; Marder, T. B. Inorg. Chim. Acta 1994, 220, 289 and references cited therein.