Ferrocenylphosphine-imine ligands for Pd-catalyzed asymmetric allylic alkylation

Tetrahedron Asymmetry

Volumn 13, Issue 15, 2002, Pages 1687-1693

  Hu, Xiangping ^a   Dai, Huicong ^a   Hu, Xinquan ^a   Chen, Huilin ^a   Wang, Junwei ^a   Bai, Changmin ^a   Zheng, Zhuo ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIPHENYLPROP 2 EN 1 YL ACETATE; ACETIC ACID DERIVATIVE; ACID; AMINE; BENZALDEHYDE DERIVATIVE; IMINE; N (2 NITROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (3 CHLOROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (3 METHOXYBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (3 NITROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (3 NITROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]PHENYLMETHYLAMINE; N (3 NITROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]PROPYLAMINE; N (4 CHLOROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (4 DIMETHYLAMINOBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (4 METHOXYBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (4 METHYLBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; N (4 NITROBENZYLIDENE) 1 [2 (DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE; PALLADIUM; PHOSPHINE DERIVATIVE; PIVALATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; PRIORITY JOURNAL; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

EID: 0037077811     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00471-8     Document Type: Article

References (57)

1. Consiglio G., Waymouth R.M. Chem. Rev. 89:1989;257-276.
2. Pfaltz A. Acc. Chem. Res. 26:1993;339-345.
3. Trost B.M., Van Vranken D.L. Chem. Rev. 96:1996;395-422.
4. Williams J.M.J. Synlett. 1996;705-710
5. Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin. 1999; Chapter 24.
6. Trost B.M., Lee C. Ojima I., Catalytic Asymmetric Synthesis. 1999;593-649 VCH, New York.
7. Hayashi T., Tajika M., Tamao K., Kumada M. J. Am. Chem. Soc. 98:1976;3718-3719.
8. Hayashi T., Fukushima M., Konishi M., Kumada M. Tetrahedron Lett. 21:1980;79-82.
9. Hayashi T., Konishi M., Fukushima M., Mise T., Kagotani M., Tajika M., Kumada M. J. Am. Chem. Soc. 104:1982;180-186.
10. Hayashi T., Konishi M., Fukushima M., Kanehira K., Hioki T., Kumada M. J. Org. Chem. 48:1983;2195-2202.
11. Kubota H., Koga K. Tetrahedron Lett. 35:1994;6689-6692.
12. Wimmer P., Widhalm M. Tetrahedron: Asymmetry. 6:1995;657-660.
13. Bourghida M., Widhalm M. Tetrahedron: Asymmetry. 9:1998;1073-1083.
14. Widhalm M., Mereiter K., Bourghida M. Tetrahedron: Asymmetry. 9:1998;2983-2986.
15. Cahill J.P., Guiry P.J. Tetrahedron: Asymmetry. 9:1998;4301-4305.
16. Anderson J.C., Cubbon R.J., Harling J.D. Tetrahedron: Asymmetry. 10:1999;2829-2832.
17. Wang Y., Guo H., Ding K. Tetrahedron: Asymmetry. 11:2000;4153-4162.
18. Stranne R., Vasse J.-L., Moberg C. Org. Lett. 3:2001;2525-2528.
19. Anderson J.C., Cubbon R.J., Harling J.D. Tetrahedron: Asymmetry. 12:2001;923-935.
20. Mino T., Tanaka Y., Akita K., Anada K., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 12:2001;1677-1682.
21. Mino T., Tanaka Y., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 12:2001;2435-2440.
22. Helmchen G., Pfaltz A. Acc. Chem. Res. 33:2000;336-345. and references cited therein.
23. Gilbertson S.R., Genov D.G., Rheingold A.L. Org. Lett. 2:2000;2885-2888.
24. Hou D.-R., Reibenspies J.H., Burgess K. J. Org. Chem. 66:2001;206-215.
25. Gilbertson S.R., Xie D., Fu Z. J. Org. Chem. 66:2001;7240-7246.
26. Deng W.-P., You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., Xia W., Sun J. J. Am. Chem. Soc. 123:2001;6508-6519.
27. You S.-L., Zhu X.-Z., Luo Y.-M., Hou X.-L., Dai L.-X. J. Am. Chem. Soc. 123:2001;7471-7472.
28. Jones G., Richards C.J. Tetrahedron Lett. 42:2001;5553-5555.
29. Ito K., Kashiwagi R., Iwasaki K., Katsuki T. Synlett. 1999;1563-1566.
30. Han J.W., Jang H.-Y., Chung Y.K. Tetrahedron: Asymmetry. 10:1999;2853-2861.
31. Ito K., Kashiwagi R., Hayashi S., Uchida T., Katsuki T. Synlett. 2001;284-286.
32. Mino T., Shiotsuki M., Yamamoto N., Suenaga T., Sakamoto M., Fujita T., Yamashita M. J. Org. Chem. 66:2001;1795-1797.
33. Saitoh A., Morimoto T., Achiwa K. Tetrahedron: Asymmetry. 8:1997;3567-3570.
34. Saitoh A., Achiwa K., Morimoto T. Tetrahedron: Asymmetry. 9:1998;741-744.
35. Saitoh A., Achiwa K., Tanaka K., Morimoto T. J. Org. Chem. 65:2000;4227-4240.
36. Jin M.-J., Jung J.-A., Kim S.-H. Tetrahedron Lett. 40:1999;5197-5198.
37. Okuyama Y., Nakano H., Hongo H. Tetrahedron: Asymmetry. 11:2000;1193-1198.
38. Mino T., Hata S., Ohtaka K., Sakamoto M., Fujita T. Tetrahedron Lett. 42:2001;4837-4839.
39. Suzuki Y., Ogata Y., Hiroi K. Tetrahedron: Asymmetry. 10:1999;1219-1222.
40. Jang H.-Y., Seo H., Han J.W., Chung Y.K. Tetrahedron Lett. 41:2000;5083-5087.
41. Kohara T., Hashimoto Y., Saigo K. Synlett. 2000;517-519.
42. Fukuda T., Takehara A., Iwao M. Tetrahedron: Asymmetry. 12:2001;2793-2799.
43. Hayashi T., Hayashi C., Uozumi Y. Tetrahedron: Asymmetry. 6:1995;2503-2506.
44. Wright J., Frambes L., Reeves P. J. Organomet. Chem. 476:1994;215-217.
45. Gokel G.W., Maequarding D., Ugi I.K. J. Org. Chem. 37:1972;3052-3058.
46. Hayashi T., Mise T., Fukushima M., Kagotani M., Nagashima N., Hamada Y., Matsumoto A., Kawakami S., Konishi M., Yamamoto K., Kumada M. Bull. Chem. Soc. Jpn. 53:1980;1138-1151.
47. von Matt P., Pfaltz A. Angew. Chem., Int. Ed. Engl. 32:1993;566-568.
48. Nomenclature note: the endo-isomer is defined here as that allyl configuration in which the central allyl proton points above the plane of the P-Pd-N chelate.
49. Farrell A., Goddard R., Guiry P.J. J. Org. Chem. 67:2002;4209-4217.
50. Akermark B., Hansson S., Krakenberger B., Vitagliano A., Zetterberg K. Organometallics. 3:1984;679-682.
51. Sprinz J., Kiefer M., Helmchen G., Resselin M. Tetrahedron Lett. 35:1994;1523-1526.
52. Allen J.V., Williams J.M.J. J. Chem. Soc., Perkin Trans. 1. 1994;2065-2072.
53. Dawson G.I., Williams J.M.J. Tetrahedron: Asymmetry. 6:1995;2535-2546.
54. Anderson J.C., James D.S., Mathias J.P. Tetrahedron: Asymmetry. 9:1998;753-756.
55. Auburn P.R., Mackenzie P.B., Bosnich B. J. Am. Chem. Soc. 107:1985;2033-2046.
56. Ohno A., Yamane M., Hayashi T., Oguni N., Hayashi M. Tetrahedron: Asymmetry. 6:1995;2495-2502.
57. Yamamoto K., Wakatsuki J., Sugimoto R. Bull. Chem. Soc. Jpn. 53:1980;1132-1137.