New chiral phosphinoimidazolidine ligand in palladium-catalyzed asymmetric allylic substitution

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7409-7411

  Jin, Myung Jong ^a   Kim, Sang Han ^a   Lee, Sang Joon ^a   Kim, Young Mok ^a  

^a Inha University   (South Korea)

Author keywords

Allylic substitution; Asymmetric catalysis; Imidazolidine ligand; Pd catalyst

Indexed keywords

1,3 DIPHENYL 2 PROPENYLACETIC ACID; ACETIC ACID DERIVATIVE; BENZYLAMINE; DIMETHYLMALONIC ACID; IMIDAZOLIDINE DERIVATIVE; MALONIC ACID DERIVATIVE; PALLADIUM; PHOSPHINOIMIDAZOLIDINE; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; RACEMIC MIXTURE; STRUCTURE ACTIVITY RELATION;

EID: 0037037905     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01676-3     Document Type: Article

References (26)

1. For recent reviews: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45; (d) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
2. For recent reviews: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45; (d) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
3. For recent reviews: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45; (d) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
4. For recent reviews: (a) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526; (b) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45; (d) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
5. Pfaltz A., Lautens M. Jacobsen E.N., Yamamoto H., Comprehensive Asymmetric Catalysis. 2:1999;833-884 Springer, Heidelberg.
6. (a) von Matt P., Pfaltz A. Angew. Chem., Int. Ed. Engl. 32:1993;566-568.
7. (b) Sprinz J., Helmchen G. Tetrahedron Lett. 34:1993;1769-1772.
8. (c) Dawson G.J., Frost C.G., Williams J.M.J., Coote S.J. Tetrahedron Lett. 34:1993;3149-3150.
9. (d) Kudis S., Helmchen G. Angew. Chem., Int. Ed. Engl. 37:1998;3047-3050.
10. (a) Ahn K.H., Cho C.-W., Park J., Lee S. Tetrahedron: Asymmetry. 8:1997;1179-1185.
11. (b) Sudo A., Yoshida H., Saigo K. Tetrahedron: Asymmetry. 8:1997;3205-3208.
12. (c) Pretot R., Pfaltz A. Angew. Chem., Int. Ed. Engl. 37:1998;323-325.
13. (d) Imai Y., Zhang W., Kida T., Nakatsuji Y., Ikeda I. Tetrahedron Lett. 39:1998;4343-4346.
14. (e) Hashimoto Y., Horie Y., Hayashi M., Saigo K. Tetrahedron: Asymmetry. 11:2000;2205.
15. (f) Mino T., Tanaka Y.-i., Akita K., Anada K., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 12:2001;1677-1682.
16. (g) Saitoh A., Achiwa K., Tanaka K., Morimoto T. J. Org. Chem. 65:2000;4227-4240.
17. (h) Fukuta T., Takehara A., Iwao M. Tetrahedron: Asymmetry. 12:2001;2793-2799.
18. (i) Ito K., Kashiwagi R., Hayashi S., Uchida T., Katsuki T. Synlett. 12:2001;284-286.
19. (j) Anderson J.C., Cubbon R.J., Harling J.D. Tetrahedron: Asymmetry. 12:2001;923-935.
20. Jin M.-J., Jung J.-A., Kim S.-H. Tetrahedron Lett. 40:1999;5197-5198.
21. 2P: C, 78.23; H, 7.54; N, 6.76. Found: C, 78.07; H, 7.61; N, 6.84%.
22. Alexakis A., Mutti S., Mangeney P. J. Org. Chem. 57:1992;1224-1237.
23. s=25.0 min).
24. (a) Hayashi T., Yamamodo A., Ito Y., Nishioka E., Miura H., Yanagi K. J. Am. Chem. Soc. 111:1989;6301-6311.
25. (b) von Matt P., Loiseleur O., Koch G., Pfaltz A. Tetrahedron: Asymmetry. 5:1994;573-584.
26. (c) Yonehara K., Hashizume T., Mori K., Ohe K., Uerura S. J. Org. Chem. 64:1999;9374-9380.