Synthesis of novel chiral bis(2-oxazolinyl)xanthene (xabox) ligands and their evaluation in catalytic asymmetric 1,3-dipolar cycloaddition reactions of nitrones with 3-crotonoyl-2-oxazolidinone

Tetrahedron Letters

Volumn 45, Issue 10, 2004, Pages 2121-2124

  Iwasa, Seiji ^a   Ishima, Yosuke ^a   Widagdo, Herman Setyo ^a   Aoki, Katsuyuki ^a   Nishiyama, Hisao ^b  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

1,3 Dipolar cycloaddition; Molecular catalyst; Nitrogen ligand; Nitrone; Xanthene backbone

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; 3 CROTONOYL 2 OXAZOLIDINONE; LEWIS ACID; MAGNESIUM DERIVATIVE; MANGANESE DERIVATIVE; NITRONE DERIVATIVE; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CYCLOADDITION; ENANTIOSELECTIVITY;

EID: 1242272933     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.043     Document Type: Article

References (44)

1. Ojima I. Catalytic Asymmetric Synthesis. 1993;VCH, New York.
2. Brunner H., Zettlmeier W. Handbook of Enantioselective Catalysis. 1993;VCH, Weinheim.
3. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley & Sons, New York.
4. Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis. 1995;John Wiley & Sons, New York.
5. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. Vols. I-III:1999;Springer, Berlin.
6. Ghosh K., Mathivanan P., Cappiello J. Tetrahedron: Asymmetry. 9:1998;1.
7. Fache F., Schulz E., Tommasino M.L., Lemaire M. Chem. Rev. 100:2000;2159.
8. Braunstein P., Naud F. Angew. Chem. Int. Ed. 40:2001;680.
9. Terfort A., Görls H., Brunner H. Synthesis. 1997;79.
10. Reetz M.T., Beuttenmuüller E.W., Goddard R. Tetrahedron Lett. 38:1997;3211.
11. Reetz M.T., Sostmann S. J. Organomet. Chem. 603:2000;105.
12. Dreher S.D., Katz T.J., Lam K.C., Rheingold A.L. J. Org. Chem. 65:2000;815.
13. Zhu Y.-Z., Li Z.-P., Ma J.-A., Tang F.-Y., Kang L., Zhou Q.-L., Chan A.S.C. Tetrahedron: Asymmetry. 13:2002;161.
14. For reviews, see: Gothelf K.V., Jørgensen K.A. Acta Chem. Scand. 50:1996;652.
15. Gothelf K.V., Jørgensen K.A. Chem. Rev. 98:1998;863.
16. Beller M., Bolm C. Transition Metals for Organic Synthesis. Vols. 1, 2:1998;Wiley-VCH, Weinheim.
17. Kanemasa S. Synlett. 2002;1371.
18. Kobayashi S., Jørgensen K.A. Cycloaddition Reactions in Organic Synthesis. 2002;274 Wiley-VCH, Weinheim.
19. Gothelf K.V., Jørgensen K.A. J. Org. Chem. 59:1994;5687.
20. Seerden J.-P.G., Scholte op Reimer A.W.A., Scheeren H.W. Tetrahedron Lett. 35:1994;4419.
21. Gothelf K.V., Thomsen I., Jørgensen K.A. J. Am. Chem. Soc. 118:1996;59.
22. Jensen K.B., Gothelf K.V., Jørgensen K.A. Helv. Chem. Acta. 80:1997;2039.
23. Sanchez-Blanco A.I., Gothelf K.V., Jørgensen K.A. Tetrahedron Lett. 38:1997;7923.
24. Kanemasa S., Oderaotoshi Y., Tanaka J., Wada E. J. Am. Chem. Soc. 120:1998;12355.
25. Kobayashi S., Kawamura M. J. Am. Chem. Soc. 120:1998;5840.
26. Ellis W.W., Gavrilova A., Sands L., Rheingold A.L., Bosnich B. Organometallics. 18:1999;332.
27. Desimoni G., Faita G., Mortoni A., Righetti P. Tetrahedron Lett. 40:1999;2001.
28. Kawamura M., Kobayashi S. Tetrahedron Lett. 40:1999;3213.
29. Simonsen K.B., Bayón P., Hazell R.G., Gothelf K.V., Jørgensen K.A. J. Am. Chem. Soc. 121:1999;3845.
30. Hori K., Komada H., Ohta T., Furukawa I. J. Org. Chem. 63:1999;5017.
31. Seebach D., Heckel A. Angew. Chem. Int. Ed. 39:2000;163.
32. Jen W.S., Wiener J.J.M., MacMillan D.W.C. J. Am. Chem. Soc. 122:2000;9874.
33. Mita T., Ohtsuki N., Ikeno T., Yamada T. Org. Lett. 4:2002;2457.
34. Kanemasa S., Ueno N., Shirahase M. Tetrahedron Lett. 43:2002;657.
35. Viton F., Bernardinelli G., Kündig E.P. J. Am. Chem. Soc. 124:2002;4968.
36. Iwasa S., Nakamura H., Nishiyama H. Heterocycles. 52:2000;939.
37. Iwasa S., Tsushima S., Shimada T., Nishiyama H. Tetrahedron Lett. 42:2001;6715.
38. Iwasa S., Tsushima S., Shimada T., Nishiyama H. Tetrahedron. 58:2002;227.
39. Iwasa S., Maeda H., Nishiyama K., Tsushima S., Tsukamoto Y., Nishiyama H. Tetrahedron. 58:2002;8281.
40. Gothelf K.V., Hazell R.G., Jørgensen K.A. J. Org. Chem. 61:1996;346.
41. Crosignani S., Desimoni G.G., Faita G., Fillippone S., Mortoni A., Righetti P., Zema M. Tetrahedron Lett. 40:1999;7007.
42. Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron. 57:2001;8313.
43. 2 in the presence of MS 4A. After the complexation, the MS was filtered off to give a pale blue solution which was again filtered via membrane filter. The catalyst solution was added to pre-activated MS 4A at room temperature followed by addition of 3-crotonoyl-2-oxazolidinone 6 and nitrone. The resulting suspension was stirred at 25 °C and the reaction was monitored by TLC. At the end of the reaction, the reaction product was directly purified by flash column chromatography on silica gel to give the desired 1,3-D.C. product.
44. 3-ether-hexane. Selected bond lengths and angle: 2.129 Å, Rh-O; 2.05 Å, Rh-N1; 2.07 Å, Rh-N2; 2.330 Å, Rh-Cl1; 2.331 Å, Rh-Cl2; 2.270 Å, Rh-Cl3; 93.8°, N1-Rh-N2; 86.9°, N1-Rh-O; 83.7°, N2-Rh-O; 89.1°, N1-Rh-Cl1; 178.2°, N1-Rh-Cl2; 91.6°, N1-Rh-Cl3; 173.7°, N2-Rh-Cl1; 86.8°, N2-Rh-Cl2; 92.1°, N2-Rh-Cl3; 90.8°, O-Rh-Cl1; 91.5°, O-Rh-Cl2; 175.5°, O-Rh-Cl3.