Catalytic asymmetric alkylation in water in the presence of surfactants: Influence of the nature of the nucleophile and the allylic acetate on the activity and enantioselectivity

Tetrahedron Asymmetry

Volumn 14, Issue 24, 2003, Pages 3891-3897

  Rabeyrin, Cedric ^a   Sinou, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIPHENYL 2 PROPENYL ACETATE; ACETIC ACID; ALKYL GROUP; ALLYL COMPOUND; BASE; BIPHENYL DERIVATIVE; CARBON; LIGAND; NITROGEN; PALLADIUM; SURFACTANT; UNCLASSIFIED DRUG; WATER;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MICELLE; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0344628649     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.09.041     Document Type: Article

References (43)

1. Cornils B., Herrmann W.A. Applied Homogeneous Catalysis with Organometallic Compounds. 1996;VCH, Weinheim.
2. Beller M., Bolm C. Transition Metals for Organic Synthesis. 1998;VCH, Weinheim.
3. Cornils B., Herrmann W.A. Aqueous-Phase Organometallic Chemistry: Concepts and Applications. 1998;VCH, Weinheim.
4. Oehme G., Paetzold E., Selke R. J. Mol. Catal. 71:1992;L1-L5.
5. Grassert I., Paetzold E., Oehme G. Tetrahedron. 49:1993;6605-6612.
6. Grassert I., Vill V., Oehme G. J. Mol. Catal. A: Chem. 116:1997;231-236.
7. Grassert I., Schmidt U., Ziegler S., Fischer C., Oehme G. Tetrahedron: Asymmetry. 9:1998;4193-4202.
8. Oehme G., Grassert I., Ziegler S., Meisel R., Fuhrmann H. Catal. Today. 42:1998;459-470.
9. Dwars T., Schmidt U., Fischer C., Grassert I., Kempe R., Fröhlich R., Drauz K., Oehme G. Angew. Chem., Int. Ed. 37:1998;2851-2853.
10. Selke R., Holz J., Riepe A., Börner A. Chem. Eur. J. 4:1998;769-771.
11. Trinkhaus S., Kadyrov R., Selke R., Holz J., Götze L., Börner A. J. Mol. Catal. A: Chem. 144:1999;15-26.
12. Oehme G., Grassert I., Paetzold E., Meisel R., Drexler K., Fuhrmann H. Coord. Chem. Rev. 185-186:1999;585-600.
13. Robert F., Oehme G., Grassert I., Sinou D. J. Mol. Catal. A: Chem. 156:2000;127-132.
14. Dwars T., Haberland J., Grassert I., Oehme G., Kragl U. J. Mol. Catal. A: Chem. 168:2001;81-86.
15. Ding H., Hanson B.E., Bakos J. Angew. Chem., Int. Ed. 34:1995;1645-1647.
16. Goedheijt M.S., Hanson B.E., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. J. Am. Chem. Soc. 122:2000;1650-1657.
17. Paetzold E., Oehme G. J. Mol. Catal. A: Chem. 152:2000;69-76.
18. Bumagin N.A., Bykov V.V., Sukhomlinova L.I., Tolstaya T.P., Beletskaya I.P. J. Organomet. Chem. 486:1995;259-262.
19. Cheparkov A.V., Ponomareva N.V., Beletskaya I.P. J. Organomet. Chem. 486:1995;297-300.
20. Badone D., Baroni M., Cardamone R., Ielmini A., Guzzi U. J. Org. Chem. 62:1997;7170-7173.
21. Manabe K., Mori Y., Wakabayashi T., Nagayama S., Kobayashi S. J. Am. Chem. Soc. 122:2000;7202-7207.
22. Uozumi Y., Danjo H., Hayashi T. Tetrahedron Lett. 38:1997;3557-3560.
23. Uozumi Y., Danjo H., Hayashi T. Tetrahedron Lett. 39:1998;8303-8306.
24. Uozumi Y., Shibatomi K. J. Am. Chem. Soc. 123:2001;2919-2920.
25. Rabeyrin C., Nguefack C., Sinou D. Tetrahedron Lett. 41:2000;7461-7464.
26. Sinou D., Rabeyrin C. Adv. Synth. Catal. 345:2003;357-363.
27. Kobayashi S., Lam W.W.-L., Manabe K. Tetrahedron Lett. 41:2000;6115-6118.
28. Yang S.C., Hung C.W. J. Org. Chem. 64:1999;5000-5001.
29. Yang S.C., Yu C.L., Tsai Y.C. Tetrahedron Lett. 41:2000;7097-7100.
30. Yang S.C., Tsai Y.C. Organometallics. 20:2001;763-770.
31. Yang S.C., Shue Y.J., Liu P.C. Organometallics. 21:2002;2013-2016.
32. Nillson Y.I.M., Andersson P.G., Bäckwall J.E. J. Am. Chem. Soc. 115:1993;6609-6613.
33. Auburn P.R., Mackenzie P.B., Bosnich B. J. Am. Chem. Soc. 107:1985;2033-2046.
34. von Matt P., Loiseleur O., Koch G., Pfaltz A., Lefeber C., Feucht T., Helmchen G. Tetrahedron: Asymmetry. 5:1994;573-584.
35. Fleming I., Higgins D., Lawrence N.J., Thomas A.P. J. Chem. Soc., Perkin Trans. 1. 1992;3331-3349.
36. Murphy J.A., Patterson C.W. J. Chem. Soc., Perkin Trans. 1. 1993;405-410.
37. Kang J., Cho W.O., Cho H.G. Tetrahedron: Asymmetry. 5:1994;1347-1352.
38. Saitoh A., Misawa M., Morimoto T. Tetrahedron: Asymmetry. 10:1999;1025-1028.
39. von Matt P., Pfaltz A. Angew. Chem., Int. Ed. Engl. 32:1993;566-568.
40. Vyskocil S., Smrcina M., Hanus V., Polasek M., Kocovsky P. J. Org. Chem. 63:1998;7738-7748.
41. Yamaguchi M., Shima T., Yamagishi T., Hida M. Tetrahedron Lett. 31:1990;5049-5057.
42. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., Yanagi K. J. Am. Chem. Soc. 111:1989;6301-6311.
43. Sudo A., Saigo K. J. Org. Chem. 62:1997;5508-5513.