Asymmetric alkylation of glycine imines using in situ generated phase-transfer catalysts

Tetrahedron Letters

Volumn 43, Issue 45, 2002, Pages 8015-8018

  Lygo, Barry ^a   Andrews, Benjamin I ^a   Crosby, John ^b   Peterson, Justine A ^c  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; GLYCINE DERIVATIVE; SODIUM CHLORIDE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; LIQUID; METHODOLOGY; PHASE TRANSITION;

EID: 0037020579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01982-2     Document Type: Article

References (41)

1. . For an authoritative review of glycine imine chemistry, see: O'Donnell M.J. Aldrichim. Acta. 34:2001;1.
2. Lygo B., Wainwright P.G. Tetrahedron Lett. 38:1997;8595.
3. Dehmlow E.V., Wagner S., Müller A. Tetrahedron. 55:1999;6335.
4. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;1385.
5. Lygo B. Tetrahedron Lett. 40:1999;1389.
6. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;8671.
7. Lygo B., Crosby J., Lowdon T.R., Wainwright P.G. Tetrahedron. 57:2001;2391.
8. Lygo B., Crosby J., Lowdon T.R., Peterson J.A., Wainwright P.G. Tetrahedron. 57:2001;2403.
9. Lygo B., Crosby J., Peterson J.A. Tetrahedron. 57:2001;6447.
10. Lygo B., Humphreys L.D. Tetrahedron Lett. 43:2001;6677.
11. Ma D., Zhang T., Wang G., Kozikowski A.P., Lewin N.E., Blumberg P.M. Bioorg. Med. Chem. Lett. 11:2001;99.
12. Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414.
13. Corey E.J., Noe M.C., Xu F. Tetrahedron Lett. 39:1998;5347.
14. Horikawa M., Busch-Petersen J., Corey E.J. Tetrahedron Lett. 40:1999;3843.
15. Boisnard S., Carbonnelle A.-C., Zhu J. Org. Lett. 3:2001;2061.
16. Jotterand N., Pearce D.A., Imperiali B. J. Am. Chem. Soc. 66:2001;3224.
17. Chen G., Deng Y., Gong L., Mi A., Cui X., Jiang Y., Choi M.C.K., Chan A.S.C. Tetrahedron: Asymmetry. 12:2001;1567.
18. Okino T., Takemoto Y. Org. Lett. 3:2001;1515.
19. (a) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775;
20. (b) O'Donnell, M. J.; Delgado, F.; Pottorf, R. S. Tetrahedron 1999, 55, 6347;
21. (c) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
22. See for example: (a) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000; (b) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097; (c) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959; (d) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2001, 3, 639.
23. See for example: (a) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000; (b) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097; (c) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959; (d) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2001, 3, 639.
24. See for example: (a) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000; (b) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097; (c) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959; (d) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2001, 3, 639.
25. See for example: (a) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000; (b) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097; (c) Perrard, T.; Plaquevent, J.-C.; Desmurs, J.-R.; Hébrault, D. Org. Lett. 2000, 2, 2959; (d) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2001, 3, 639.
26. Lygo B., Wainwright P.G. Tetrahedron Lett. 39:1998;1599.
27. Lygo B., Wainwright P.G. Tetrahedron. 55:1999;6289.
28. Lygo B., To D.C.M. Tetrahedron Lett. 42:2001;1343.
29. See for example: (a) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745; (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; (c) Jew, S. S.; Jeong, B. S.; Yoo, M. S.; Huh, H.; Park, H. G. Chem. Commun. 2001, 1244; (d) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Park, M. K.; Huh, H.; Jew, S. S. Tetrahedron Lett. 2001, 42, 4645; (e) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
30. See for example: (a) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745; (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; (c) Jew, S. S.; Jeong, B. S.; Yoo, M. S.; Huh, H.; Park, H. G. Chem. Commun. 2001, 1244; (d) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Park, M. K.; Huh, H.; Jew, S. S. Tetrahedron Lett. 2001, 42, 4645; (e) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
31. See for example: (a) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745; (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; (c) Jew, S. S.; Jeong, B. S.; Yoo, M. S.; Huh, H.; Park, H. G. Chem. Commun. 2001, 1244; (d) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Park, M. K.; Huh, H.; Jew, S. S. Tetrahedron Lett. 2001, 42, 4645; (e) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
32. See for example: (a) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745; (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; (c) Jew, S. S.; Jeong, B. S.; Yoo, M. S.; Huh, H.; Park, H. G. Chem. Commun. 2001, 1244; (d) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Park, M. K.; Huh, H.; Jew, S. S. Tetrahedron Lett. 2001, 42, 4645; (e) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
33. See for example: (a) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745; (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; (c) Jew, S. S.; Jeong, B. S.; Yoo, M. S.; Huh, H.; Park, H. G. Chem. Commun. 2001, 1244; (d) Park, H. G.; Jeong, B. S.; Yoo, M. S.; Park, M. K.; Huh, H.; Jew, S. S. Tetrahedron Lett. 2001, 42, 4645; (e) Thierry, B.; Plaquevent, J. C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
34. O'Donnell M.J., Wu S., Huffman J.C. Tetrahedron. 50:1994;4507.
35. Fernandez M.-J., Gude L., Lorente A. Tetrahedron Lett. 42:2001;891.
36. For applications of anthracenylmethyl glycine derivatives, see: (a) Nestor, J. J.; Ho, T. L.; Simpson, R. A.; Horner, B. L.; Jones, G. H.; McRae, G. I.; Vickery, B. H. J. Med. Chem. 1982, 25, 795; (b) Hohsaka, T.; Kajihara, D.; Ashizuka, Y.; Murakami, H.; Sisido, M. J. Am. Chem. Soc. 1999, 121, 34.
37. For applications of anthracenylmethyl glycine derivatives, see: (a) Nestor, J. J.; Ho, T. L.; Simpson, R. A.; Horner, B. L.; Jones, G. H.; McRae, G. I.; Vickery, B. H. J. Med. Chem. 1982, 25, 795; (b) Hohsaka, T.; Kajihara, D.; Ashizuka, Y.; Murakami, H.; Sisido, M. J. Am. Chem. Soc. 1999, 121, 34.
38. Sufficent dichloromethane was added so as to give a final toluene:dichloromethane ratio of 7:3. This solvent ratio has previously been reported to be optimal for alkylations of this type, see: Esikova, I. A.; Nahreini, T. S.; O'Donnell, M. J. In ACS Symposium Series 659: Phase-Transfer Catalysis - Mechanisms and Syntheses; Halpern, M. E., Ed.; ACS: Washington, DC, 1997; p. 89.
39. 1H NMR) for use in subsequent reactions.
40. This value is the average e.e. (four runs) obtained using catalyst 1 (R=Bn, X=Br) generated in situ. When pre-prepared catalyst was used under similar conditions, imine 8 was obtained in 93% e.e.
41. The aqueous phase was saturated with KBr in order to prevent freezing.