First application of chiral ionic liquids in asymmetric Baylis-Hillman reaction

Tetrahedron Letters

Volumn 45, Issue 34, 2004, Pages 6425-6428

  Pégot, Bruce ^a   Vo Thanh, Giang ^a   Gori, Didier ^a   Loupy, André ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Asymmetric synthesis; Baylis Hillman reaction; Chirality; Ionic liquids

Indexed keywords

EPHEDRINE DERIVATIVE; ION;

ARTICLE; ASYMMETRIC SYNTHESIS; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; LIQUID; QUANTUM YIELD;

EID: 4143095848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.134     Document Type: Article

References (30)

1. T. Welton Chem. Rev. 99 1999 2071 2083
2. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
3. R. Sheldon Chem. Commun. 2001 2399 2407
4. P. Wasserscheid T. Welton Ionic Liquids in Synthesis 2002 Wiley-VCH
5. (e) Ionic Liquids Industrial Applications to Green Chemistry. In Rogers, R. D.; Seddon, K. R. Eds.; ACS, Symposium Series 818, 2001
6. For a review on the chiral ionic liquids, see: C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, and J.-C. Plaquevent Tetrahedron: Asymmetry 14 2003 3081 3093
7. M.J. Earle, P.B. McCormac, and K.R. Seddon Green Chem. 1 1999 23 25
8. J. Howarth, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097 3100
9. P. Wasserscheid, A. Bösmann, and C. Bolm Chem. Commun. 2002 200 201
10. G. Vo-Thanh, B. Pégot, and A. Loupy Eur. J. Org. Chem. 5 2004 1112 1116
11. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
12. I.E. Markó, P.R. Giles, and N.J. Hindley Tetrahedron 53 1997 1015 1024
13. T. Oishi, H. Oguri, and M. Hirama Tetrahedron: Asymmetry 6 1995 1241 1244
14. Y. Iwabuchi, M. Nakatani, N. Yokoyama, and S. Hatakeyama J. Am. Chem. Soc. 121 1999 10219 10220
15. S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, and S. Hatakeyama Org. Lett. 5 2003 3103 3105
16. K.-S. Yang, W.-D. Lee, J.-F. Pan, and K. Chen J. Org. Chem. 68 2003 915 919
17. D. Seebach, and H. Oei Angew. Chem., Int. Ed. Engl. 14 1975 634 636
18. J. March, and M.B. Smith Advanced Organic Chemistry 2001 Wiley-Interscience p 150
19. O. Ulbert, A. Szarka, S. Halasi, B. Somogyi, K. Bélafi- Bakó, and L. Gubicza Biotechnol. Tech. 13 1999 299 302
20. V.K. Aggarwal, I. Emme, and A. Mereu Chem. Commun. 2002 1612 1613
21. E.J. Kim, S.Y. Ko, and C.E. Song Helv. Chim. Acta 86 2003 894 899
22. A. Kumar, and S.S. Pawar J. Mol. Catal. A 211 2004 43 47
23. J.-C. Hsu, Y.-H. Yen, and Y.-H. Chu Tetrahedron Lett. 45 2004 4673 4676
24. The ee value was determined by chiral HPLC analysis of 1 (Ar = Ph). Separation conditions: (S,S)-Whelk-01 column 4.6 mm x 250 mm (thermostatted column 0-1°C); elution with a mixture of hexane/ethanol 99/1; flow rate 1 mL/min; retention time 28 min for (R)-1 and 33 min for (S)-1 enantiomer
25. S.E. Drewes, N.D. Emslie, J.S. Field, A.A. Kahn, and N. Ramesar Tetrahedron: Asymmetry 3 1992 255 260
26. R.P. Swatloski, J.D. Holbrey, and R.D. Roger Green Chem. 5 2003 361 363
27. J. Balcells, S. Colonna, and R. Fornasier Synthesis 1976 266 267
28. S. Colonna, and R. Fornasier J. C. S. Perkin Trans. 1 1978 371 373
29. A. Loupy, and A. Zaparucha Tetrahedron Lett. 34 1993 473 476
30. E. Diez-Barra, and A. de la Hoz Y. Diez-Barra Sasson Handbook of Phase Transfer Catalysis 1997 Blackie Academic and Professional London pp 276-316