Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams

Journal of the American Chemical Society

Volumn 127, Issue 4, 2005, Pages 1206-1215

  France, Stefan ^a   Shah, Meha H ^a   Weatherwax, Anthony ^a   Wack, Harald ^a   Roth, Justine P ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSTS; DERIVATIVES; ORGANIC ACIDS; STEREOCHEMISTRY;

BIFUNCTIONAL CATALYSTS; CHEMICAL YIELD; CHIRAL NUCLEOPHILES; ENANTIOSELECTIVITY;

CATALYSIS;

ALUMINUM; BETA LACTAM; CINCHONA ALKALOID; ENOLASE; IMINE; INDIUM; LEWIS ACID; LEWIS BASE; SCANDIUM; ZINC;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

ALUMINUM; BETA-LACTAMS; CATALYSIS; CINCHONA ALKALOIDS; IMINES; INDIUM; METALS; MODELS, MOLECULAR; SCANDIUM; STEREOISOMERISM; ZINC;

EID: 13644264785     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044179f     Document Type: Article

References (67)

1. (a) Murray, G. I. J. Pathol. 2001, 195, 135-137.
2. (b) Huang, X.; Holden, H. M.; Raushel, F. M. Annu. Rev. Biochem. 2001, 70, 149-180.
3. (a) Kim, D. H.; Mobashery, S. Curr. Med. Chem. 2001, 8, 959-965.
4. (b) Auld, D. S. Astacins 1997, 119-131.
5. (c) Monetcucco, C.; Schiavo, G. Trends Biochem. Sci. 1993, 18, 324-327.
6. Bifunctional catalysis has often been defined as involving a mechanism in which two functional catalysts (in this case a Lewis base and Lewis acid) are involved in the rate-determining step, such that rate enhancement is observed. The term concerted catalysis has also been proposed to describe the simultaneous action of two catalysts and could be applied to a variant of our system reported herein. (a) Swain, C. G.; Brown, J. F., Jr. J. Am. Chem. Soc. 1952, 74, 2538-2543. (b) DiMauro, E. F.; Mamai, A.; Kozlowski, M. C. Organometallics 2003, 22, 850-855.
7. Bifunctional catalysis has often been defined as involving a mechanism in which two functional catalysts (in this case a Lewis base and Lewis acid) are involved in the rate-determining step, such that rate enhancement is observed. The term concerted catalysis has also been proposed to describe the simultaneous action of two catalysts and could be applied to a variant of our system reported herein. (a) Swain, C. G.; Brown, J. F., Jr. J. Am. Chem. Soc. 1952, 74, 2538-2543. (b) DiMauro, E. F.; Mamai, A.; Kozlowski, M. C. Organometallics 2003, 22, 850-855.
8. (a) Groger, H. Chem. - Eur. J. 2001, 7, 5247-5257.
9. (b) Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
10. (c) Steinhagen, H.; Helmchem, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2339-2342.
11. (d) Jaeschke, G.; Seebach, D. J. Org. Chem. 1998, 63, 1190-1197.
12. (a) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
13. (b) Woolley, P. J. Chem. Soc., Chem. Commun. 1975, 14, 579-580.
14. (c) Dong, S. D.; Breslow, R. Tetrahedron Lett. 1998, 39, 9343-9346.
15. (d) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
16. France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Org. Lett. 2002, 4, 1603-1605.
17. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533-3539.
18. (a) Aggarwal, V. J. Org. Chem. 1998, 63, 7183-7189.
19. (b) Aggarwal, V. J. Org. Chem. 2002, 67, 510-514.
20. Shi, M.; Jiang, J.-K. Tetrahedron: Asymmetry 2002, 13, 1941-1947.
21. Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Org. Lett. 2003, 5, 949-952.
22. Wadamoto, M.; Ozasa, N.; Yanagisawa, A.; Yamamoto, H. J. Org. Chem. 2003, 68, 5593-5601.
23. (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.
24. (b) Nogami, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2003, 51, 702-709.
25. Baeza, A.; Casas, J.; Najera, C.; Sansano, J. M.; Saa, J. M. Angew. Chem., Int. Ed. 2003, 42, 3143-3146.
26. Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594-11599.
27. DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781-3784.
28. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A. Eur. J. Org. Chem. 2003, 8, 1428-1432.
29. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
30. (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
31. (b) Ferraris, D.; Young, B.; Cox, C.; Drury, W. J., III; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090-6091.
32. (c) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006-11007.
33. (d) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168-2169.
34. (a) Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547-2548.
35. (b) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844-4849.
36. (c) Saaby, A.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4115.
37. (d) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. - Eur. J. 2000, 6, 2435-2448.
38. Standard reaction conditions consisted of 10 mol % BQ 3a, 1 equiv of proton sponge as a stoichiometric base, 1 equiv of imino ester 5a, and 1 equiv of acid chloride in toluene at -78°C.
39. For a recent review on indium-catalyzed reactions, see the following: Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015-3019.
40. 2-symmetric bis(cyclophane diol) ligand and its application toward improving the diastereoselectivity of our bifunctional system: Wack, H.; France, S.; Hafez, A. M.; Drury, W. J., III; Weatherwax, A.; Lectka, T. J. Org. Chem. 2004, 69, 4531-4533.
41. 3 as a cocatalyst.
42. Carty, A. J.; Tuck, D. G. Prog. Inorg. Chem. 1975, 19, 243-337.
43. Chung, H. L.; Tuck, D. G. Can. J. Chem. 1974, 52, 3944-3949.
44. Ranu, B. C. Eur. J. Org. Chem. 2000, 2347-2356.
45. Paver, M. A.; Russell, C. A.; Wright, D. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science: New York, 1995; Vol. 1, Chapter 11.
46. 3 in THF (a solvent in which it is fully soluble).
47. Tuck, D. G. Coord. Chem. Rev. 1966, 1, 286-291.
48. (b) Tuck, D. G. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1987; Vol. 3, Chapter 25.2.
49. (c) Pedrosa de Jesus, J. D. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1987; Vol. 2, Chapter 15.7.
50. Gillard, R. D.; Vaughan, D. H. Transition Met. Chem. 1978, 3, 44-48.
51. (a) Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920-3922.
52. (b) Chavez, I.; Alvarez-Carena, A.; Molins, E.; Roig, A.; Maniukiewicz, W.; Arancibia, A.; Arancibia, V.; Brand, H.; Manuel Manriquez, J. J. Organomet. Chem. 2000, 601, 126-132.
53. Nishida, H.; Takada, N.; Yoshimura, M. Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604.
54. See Supporting Information for details.
55. 3 standard.
56. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626-6635.
57. Taggi, A. E.; Wack, H.; Hafez, A. M.; France, S.; Lectka, T. Org. Lett. 2002, 4, 627-629.
58. Conversions as close to 20% as possible were measured to negate the effect of product inhibition and catalyst degradation (which may occur through acylation of the phenolic oxygen).
59. Due to the number of potential manifolds in our reaction pathway, no one step can be defined as the only rate-determining step. The calculated KIE should be considered as an aggregate resulting from an ensemble of RDS's, which is in fact a common but underappreciated occurrence in complex chemical reactions.
60. We have previously found that imine 5a can be activated by late transition metal chiral bis(phosphine) complexes to catalyze the enantio- and diastereoselective addition of various nucleophiles: Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
61. It is possible that the metal salt rather than catalyzing the formation of product suppresses the formation of undesired side products.
62. (a) Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415-5423.
63. (b) Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1999, 16, 2293-2297.
64. Wynberg, H.; Staring, E. G. J. Am. Chem. Soc. 1982, 104, 166-168.
65. (a) France, S.; Wack, H.; Taggi, A. E.; Hafez, A. M.; Wagerle, T. R.; Shah, M. H.; Dusich, C. L.; Lectka, T. J. Am. Chem. Soc. 2004, 126, 4245-4255.
66. (b) Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531-1532.
67. 3 and the imine (1 mL of toluene) was added via syringe pump over 1 h.