Chiral pyrrolidine thioethers: Effective nitrogen-sulfur donating ligands in palladium-catalyzed asymmetric allylic alkylations

Tetrahedron Asymmetry

Volumn 15, Issue 9, 2004, Pages 1437-1444

  Siedlecka, Renata ^a   Wojaczyńska, Elzbieta ^a   Skarzewski, Jacek ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; MALONIC ACID DERIVATIVE; NITROGEN; PALLADIUM COMPLEX; PYRROLIDINE DERIVATIVE; SULFIDE; SULFUR;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY; TRANS ISOMER;

EID: 2342429657     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.03.015     Document Type: Article

References (36)

1. Ojima I. Catalysis in Asymmetric Synthesis. 2nd ed. 2000;Wiley-VCH, New York
2. For reviews, see: Pfaltz A., Lautens M. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vol. II:1999;833-884 Springer, Berlin
3. Trost B.M., Van Vranken D.L. Chem. Rev. 96:1996;395-422
4. Trost B.M., Crawley M.L. Chem. Rev. 103:2003;2921-2944
5. Handy S.T. Curr. Org. Chem. 4:2000;363-395
6. Whitesell J.K. Chem. Rev. 89:1989;1581-1590
7. Trost B.M. Acc. Chem. Res. 29:1996;355-364
8. Pfaltz A. Acc. Chem. Res. 26:1993;339-345
9. Pfaltz A. Synlett. 1999;835-842
10. Szabo K.J. Organometallics. 15:1996;1128-1133
11. For recent examples of the P, N-ligands, see: Helmchen G., Pfaltz A. Acc. Chem. Res. 33:2000;336-345
12. Constantine R.N., Kim N., Bunt R.C. Org. Lett. 5:2003;2279-2282
13. P, S-ligands: Nakano H., Okuyama Y., Yamagida M., Hongo H. J. Org. Chem. 66:2001;620-625
14. N, S-ligands: Adams H., Anderson J.C., Cubbon R., James D.S., Mathias J.P. J. Org. Chem. 64:1999;8256-8262
15. Jansat S., Gómez M., Muller G., Diéguez M., Aghmiz A., Claver C., Masdeu-Bultó A.M., Flores-Santos L., Martin E., Maestro M.A., Mahia J. Tetrahedron: Asymmetry. 12:2001;1469-1474
16. For reviews on the catalytical use of sulfur containing ligands, see: Bayón J.C., Claver C., Masdeu-Bultó A.M. Coord. Chem. Rev. 193-195:1999;73-145
17. Masdeu-Bultó A.M., Diéguez M., Martin E., Gómez M. Coord. Chem. Rev. 242:2003;159-201
18. For the most recent example, see: Khiar N., Araújo C.S., Alvarez E., Fernández I. Tetrahedron Lett. 44:2003;3401-3404
19. Skarżewski J., Gupta A., Wojaczyńska E., Siedlecka R. Synlett. 2003;1615-1619
20. Hata T., Sekine M. Chem. Lett. 1974;837-838
21. For a review, see: Valentine D.H., Hillhouse J.H. Synthesis. 2003;317-334
22. Siedlecka R., Skarżewski J. Synlett. 1996;757-758
23. Cardona F., Goti A., Picasso S., Vogel P., Brandi A. J. Carbohydr. Chem. 19:2000;585-601
24. Cran G.A., Gibson C.L., Handa S. Tetrahedron: Asymmetry. 6:1995;1553-1556
25. Canle L.M., Clegg W., Demirtas I., Elsegood M.R.J., Maskill H. J. Chem. Soc., Perkin Trans. 2. 2000;85-92
26. Skarżewski J., Ostrycharz E., Siedlecka R. Tetrahedron: Asymmetry. 10:1999;3457-3461
27. Mislow K., Green M.M., Laur P., Melillo J.T., Simmons T., Ternay A.L. J. Am. Chem. Soc. 87:1965;1958-1976
28. Rosini C., Donnoli M.I., Superchi S. Chem. Eur. J. 7:2001;72-79
29. Tokunoh R., Sodeoka M., Aoe K., Shibasaki M. Tetrahedron Lett. 36:1995;8035-8038
30. Rassias G.A., Page P.C.B., Reignier S., Christie S.D.R. Synlett. 2000;379-381
31. Page P.C.B., Heaney H., Reignier S., Rassias G.A. Synlett. 2003;22-28
32. Hutton A.T. Wilkinson G. Comprehensive Coordination Chemistry. Vol. 5:1987;1131-1155 Pergamon, Oxford
33. Müller A., Diemann E. Wilkinson G. Comprehensive Coordination Chemistry. Vol. 2:1987;551-558 Pergamon, Oxford
34. Sprintz J., Helmchen G. Tetrahedron Lett. 34:1993;1769
35. Leutenegger U., Umbricht G., Fahrni C., Von Matt P., Pfaltz A. Tetrahedron. 48:1992;2143-2156
36. Hayashi T., Yamamoto A., Hagihara T., Ito Y. Tetrahedron Lett. 27:1986;191-194