Asymmetric addition of organolithium reagents to prochiral arene tricarbonylchromium complexes

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2258-2259

  Amurrio, David ^a   Khan, Karl ^a   Kündig, E Peter ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5244362549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960070h     Document Type: Article

References (25)

1. For reviews see: (a) Tomioka, K. Synthesis 1990, 541. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. For recent reports of additions to imines see: (c) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (d) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429.
2. For reviews see: (a) Tomioka, K. Synthesis 1990, 541. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. For recent reports of additions to imines see: (c) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (d) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429.
3. For reviews see: (a) Tomioka, K. Synthesis 1990, 541. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. For recent reports of additions to imines see: (c) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (d) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429.
4. For reviews see: (a) Tomioka, K. Synthesis 1990, 541. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. For recent reports of additions to imines see: (c) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797. (d) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429.
5. (a) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
6. (b) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681.
7. Birch reduction/alkylation of benzoic acid derivatives: For a review see (a) Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1. For chiral examples see: (b) Schultz, A. G.; Macielag, M.; Sundararaman, P.; Taveras, A. G.; Welch, M. J. Am. Chem. Soc. 1988, 110, 7828 and references cited therein.
8. Birch reduction/alkylation of benzoic acid derivatives: For a review see (a) Rabideau, P. W.; Marcinow, Z. Org. React. 1992, 42, 1. For chiral examples see: (b) Schultz, A. G.; Macielag, M.; Sundararaman, P.; Taveras, A. G.; Welch, M. J. Am. Chem. Soc. 1988, 110, 7828 and references cited therein.
9. 3 complexes see: Semmelhack, M. F. In Comprehensive Organometallic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, p 517.
10. (a) Kundig, E. P.; Cunningham, A. F., Jr.; Paglia, P.; Simmons, D. P. Helv. Chim. Acta 1990, 73, 386.
11. (b) Kundig, E. P.; Inage, M.; Bernadinelli, G. Organometallics 1991, 10, 2921.
12. Kundig, E. P.; Ripa, A.; Liu, R.; Bernardinelli, G. J. Org. Chem. 1994, 59, 4773.
13. Kundig, E. P.; Ripa, A.; Bernardinelli, G. Angew. Chem., Intl. Ed. Engl. 1992, 31, 1071.
14. (-)-Sparteine (3): Fluka. For a recent example of the catalytic use of sparteine in asymmetric additions to aldehyde imines see ref 1c. For recent references of the use of sparteine in enantioselective deprotonations see: (a) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231. (b) Guarnieri, W.; Grehl, M.; Hoppe, D. Angew. Chem., Intl. Ed. Engl. 1994, 33, 1734.
15. (-)-Sparteine (3): Fluka. For a recent example of the catalytic use of sparteine in asymmetric additions to aldehyde imines see ref 1c. For recent references of the use of sparteine in enantioselective deprotonations see: (a) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231. (b) Guarnieri, W.; Grehl, M.; Hoppe, D. Angew. Chem., Intl. Ed. Engl. 1994, 33, 1734.
16. Ether (1R,2R)-4, (1S,2S)-5, and (1S,2S)-6 were obtained in high yield from the diols (1R,2R)-9, (1S,2S)-10, and (1S,2S)-11, respectively (all >99% ee), by reaction with NaH and dimethyl sulfate, (a) Diol (1R,2R)-9 is available commercially (Fluka). (b) Diol (1S,2S)-10 was obtained by a literature procedure: Seemayer, R., Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 49. (c) Diol (1S,2S)-11 was obtained by a literature procedure: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (d) For previous application of 4 and 6 as chiral ligands for organolithium reagent additions to naphthalenes see ref 2.
17. Ether (1R,2R)-4, (1S,2S)-5, and (1S,2S)-6 were obtained in high yield from the diols (1R,2R)-9, (1S,2S)-10, and (1S,2S)-11, respectively (all >99% ee), by reaction with NaH and dimethyl sulfate, (a) Diol (1R,2R)-9 is available commercially (Fluka). (b) Diol (1S,2S)-10 was obtained by a literature procedure: Seemayer, R., Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 49. (c) Diol (1S,2S)-11 was obtained by a literature procedure: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (d) For previous application of 4 and 6 as chiral ligands for organolithium reagent additions to naphthalenes see ref 2.
18. Ether (1R,2R)-4, (1S,2S)-5, and (1S,2S)-6 were obtained in high yield from the diols (1R,2R)-9, (1S,2S)-10, and (1S,2S)-11, respectively (all >99% ee), by reaction with NaH and dimethyl sulfate, (a) Diol (1R,2R)-9 is available commercially (Fluka). (b) Diol (1S,2S)-10 was obtained by a literature procedure: Seemayer, R., Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 49. (c) Diol (1S,2S)-11 was obtained by a literature procedure: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (d) For previous application of 4 and 6 as chiral ligands for organolithium reagent additions to naphthalenes see ref 2.
19. Ether (1R,2R)-4, (1S,2S)-5, and (1S,2S)-6 were obtained in high yield from the diols (1R,2R)-9, (1S,2S)-10, and (1S,2S)-11, respectively (all >99% ee), by reaction with NaH and dimethyl sulfate, (a) Diol (1R,2R)-9 is available commercially (Fluka). (b) Diol (1S,2S)-10 was obtained by a literature procedure: Seemayer, R., Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 49. (c) Diol (1S,2S)-11 was obtained by a literature procedure: Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. (d) For previous application of 4 and 6 as chiral ligands for organolithium reagent additions to naphthalenes see ref 2.
20. 3 complexes by alkyl Li reagents/chiral ligands or by chiral amide bases see: (a) Price, D. A.; Simpkins, N S.; MacLeod, A. M.; Watt, A. P. J. Org. Chem. 1994, 59, 1961. b) Kundig, E. P.; Quattropani, A. Tetrahedron Lett. 1994, 35, 3497. (c) Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron Asymm. 1994, 5, 1427. (d) Schmalz, H. G.; Schellhaas, K. Tetrahedron Lett. 1995, 36, 5515
21. 3 complexes by alkyl Li reagents/chiral ligands or by chiral amide bases see: (a) Price, D. A.; Simpkins, N S.; MacLeod, A. M.; Watt, A. P. J. Org. Chem. 1994, 59, 1961. b) Kundig, E. P.; Quattropani, A. Tetrahedron Lett. 1994, 35, 3497. (c) Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron Asymm. 1994, 5, 1427. (d) Schmalz, H. G.; Schellhaas, K. Tetrahedron Lett. 1995, 36, 5515
22. 3 complexes by alkyl Li reagents/chiral ligands or by chiral amide bases see: (a) Price, D. A.; Simpkins, N S.; MacLeod, A. M.; Watt, A. P. J. Org. Chem. 1994, 59, 1961. b) Kundig, E. P.; Quattropani, A. Tetrahedron Lett. 1994, 35, 3497. (c) Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron Asymm. 1994, 5, 1427. (d) Schmalz, H. G.; Schellhaas, K. Tetrahedron Lett. 1995, 36, 5515
23. 3 complexes by alkyl Li reagents/chiral ligands or by chiral amide bases see: (a) Price, D. A.; Simpkins, N S.; MacLeod, A. M.; Watt, A. P. J. Org. Chem. 1994, 59, 1961. b) Kundig, E. P.; Quattropani, A. Tetrahedron Lett. 1994, 35, 3497. (c) Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron Asymm. 1994, 5, 1427. (d) Schmalz, H. G.; Schellhaas, K. Tetrahedron Lett. 1995, 36, 5515
24. 3 complexes, but compared to imines, hydrazones are far more resistant to nonoxidative hydrolyis. Kundig, E. P.; Liu, R.; Ripa, A. Helv. Chim. Acta 1992, 75, 2675.
25. Enantioselectivities need to be high though. A significant convenience of diastereoselective reactions lies in the easy product separation of diastereomeric products.