Highly efficient asymmetric alkylation and allylation of N-(diphenylmethylene)glycine tert-butyl ester with a chiral phase-transfer catalyst

Chemtracts

Volumn 15, Issue 9, 2002, Pages 498-505

  Poli, Giovanni ^a   Madec, David ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE; CINCHONA ALKALOID; GLYCINE DERIVATIVE; N (DIPHENYLMETHYLENE)GLYCINE TERT BUTYL ESTER; PALLADIUM; SCHIFF BASE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; PHASE TRANSITION; REVIEW;

EID: 0036669364     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (42)

1. (a) Demlow, E.V., Demlow, S.S. Phase Transfer Catalysis, 3rd Ed., VCH: Weinheim, 1993;
2. (b) Goldberg, Y. Phase Transfer Catalysis: Selected Problems and Applications, Gordon & Breach: Reading, 1992;
3. (c) Straks, C.M., Liotta, C.L., Halpern, M. Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives, Chapman-Hall: New York, 1994;
4. (d) Shioiri, T. In Handbook of Phase Transfer Catalysis, Sasson, Y. Neumann, R., eds., Blackie Academic & Professional: London, 1997, chap. 14;
5. (e) Nelson, A. Angew. Chem. Int. Ed. Engl. 1999, 38, 1583;
6. (f) Halpern, M.E. In Process Chemistry in the Pharmaceutical Industry, Dekker, M., ed., 1999, p. 283;
7. (g) Shioiri, T., Arai, S. Asymmetric Phase Transfer Catalysis in Stimulating Concepts in Chemistry, Vögtle, F., Stoddart, J.F., Shibasaki, M. eds., New York: Wiley-VCH, 2000.
8. (a) Wynberg, H. Chemtech. 1982, 12, 116;
9. (b) Gasparski, C.M., Miller, M.J. Tetrahedron 1991, 47, 5367;
10. (c) Conn, R.S.E., Lovell, A.V., Karady, S., Weinstock, L.M. J. Org. Chem. 1986, 51, 4710;
11. (d) Arai, S., Oku, M., Ishida, T., Shiori, T. Tetrahedron Lett. 1999, 40, 6785;
12. (e) Arai, S., Shirai, Y., Ishida, T., Shiori, T. Tetrahedron 1999, 55, 6375;
13. (f) Arai, S., Nakayama, K., Ishida, T., Shiori, T. Tetrahedron Lett. 1999, 40, 4215;
14. (g) Hintermann, L., Togni, A. Angew. Chem. Int. Ed. Engl. 2000, 39, 4359;
15. (h) Cahard, D., Audouard, C., Plaquevent, J.-C., Roques, N. Org. Lett. 2000, 2, 3699;
16. (i) Ooi, T., Takeuchi, M., Kameda, M., Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228;
17. (j) Perrard, T., Plaquevent, J.-C., Desmurs, J.-R., Hébrault, D. Org. Lett. 2000, 2, 2959;
18. (k) O'Donnell, M. Aldrichimica Acta 2001, 34, 3;
19. (l) Kim, D.Y., Huh, S.C., Kim, S.M. Tetrahedron Lett. 2001, 42, 6299;
20. (m) Park, H.-G., Jeong, B.-S., Yoo, M.-S., Park, M.-K., Huh, H., Jew, S.-S. Tetrahedron Lett. 2001, 42, 4645;
21. (n) Mohar, B., Baudoux, J., Plaquevent, J.-C., Cahard, D. Angew. Chem., Int. Ed. Engl. 2001, 40, 4214;
22. (o) Special Topic: Reactions Mediated by Cinchona Alkaloids: Carreira, E.M., ed. Synthesis 2001, 1716;
23. (p) Muniz, K. Angew. Chem. Int. Ed. Engl. 2001, 40, 1653;
24. (q) Kim, D.Y., Park, E.J. Org. Lett. 2002, 4, 545.
25. Fiaud, J.-C. Tetrahedron Lett. 1975, 40, 3495.
26. Dolling, U.-H., Davis, P., Grabowski, E.J.J. J. Am. Chem. Soc. 1984, 106, 446.
27. (a) Genêt, J.P., Juge, S., Besnier, I., Uziel, J., Ferroud, D., Kardos, N., Achi, S., Ruiz-Montes, J., Thorimbert, S. Bull. Soc. Chim. Fr. 1990, 127, 781;
28. (b) Hiroi, K., Hidaka, A., Sezaki, R., Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769;
29. (c) Baldwin, I.C., Williams, J.M.J., Beckett, R.P. Tetrahedron: Asymmetry 1995, 6, 1515.
30. O'Donnell, M.J., Bennett, W.D., Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
31. (a) O'Donnell, M.J., Wu, S., Huffman, J.C. Tetrahedron 1994, 50, 4507;
32. (b) O'Donnell, M.J., Delgado, F., Hostettler, C., Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775.
33. (a) Corey, E.J., Xu, F., Noe, M.C. J. Am. Chem. Soc. 1997, 119, 12414;
34. (b) Corey, E.J., Bo, Y., Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000;
35. (c) Corey, E.J., Xu, F., Noe, M.C. Tetrahedron Lett. 1998, 39, 5347.
36. (a) Lygo, B., Wainwright, P.G. Tetrahedron Lett. 1997, 38, 8595;
37. (b) Lygo, B., Crosby, J., Peterson, J.A. Tetrahedron Lett. 1999, 40, 8671.
38. Chinchilla, R., Mazon, P., Nájera, C. Tetrahedron: Asymmetry 2000, 11, 3277.
39. For an example of asymmetric Michael addition by solid-liquid phase transfer catalysis without solvent, see: Loupy, A., Sansoulet, J., Zaparucha, A., Merienne, C. Tetrahedron Lett. 1989, 30, 333.
40. Poli, G., Scolastico, C. Chemtracts-Org. Chem. 1999, 12, 837.
41. Kuhn, O., Mayr, H. Angew. Chem. Int. Ed. Engl. 1999, 38, 343.
42. Frost, C.G., Howarth, J., Williams, J.M.J. Tetrahedron: Asymmetry 1992, 3, 1089.