Application of (S, S)-pentacycloundecane bis(4-phenyloxazoline) as a novel chiral ligand for catalysis of the asymmetric diels-alder reaction of cyclopentadiene with 3-acryloyl-2-oxazolidinone

South African Journal of Chemistry

Volumn 62, Issue , 2009, Pages 60-66

  Arvidsson, Per I ^a   Govender, Thavendran ^b   Kruger, Hendrik G ^b   Maguire, Glenn E M ^b   Naicker, Tricia ^b  

^a UPPSALA UNIVERSITY   (Sweden)

^b UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

Chiral catalysis; Diels alder reaction; Oxazolines; Pentacycloundecane

Indexed keywords

EID: 77952934040     PISSN: 03794350     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. R. Noyori, Angew. Chem., Int. Ed. Engl., 2002, 41, 2008-2022.
2. J. Halpern and B.M. Trost, Proc. Nat. Acad. Sci., 2004, 101, 5347.
3. B.M. Trost, Proc. Nat. Acad. Sci., 2004, 101, 5348-5355.
4. G. Desimoni, G. Faita and K.A. Jorgensen, Chem. Rev., 2006, 106, 3561-3651.
5. A.K. Ghosh, M. Packiarajan and J. Cappiello, Tetrahedron-Asymmetry, 1998, 9, 1-45.
6. M. Gomez, G. Muller and M. Rocamora, Coord. Chem. Rev., 1999, 193-195, 769-835.
7. H.A. McManus and P.J. Gurry, Chem. Rev., 2004, 104, 4151-4202.
8. A.P. Marchand, H.S. Chong and B. Ganguly, Tetrahedron-Asymmetry, 1999, 10, 4695-4700.
9. G.A. Boyle, T. Govender, H.G. Kruger and G.E.M. Maguire, Tetrahedron-Asymmetry, 2004, 15, 3775-3781.
10. G.A. Boyle, T. Govender, H.G. Kruger and G.E.M. Maguire, Tetrahedron-Asymmetry, 2004, 15, 2661-2666.
11. G.A. Boyle, T. Govender, H.G. Kruger, G.E.M. Maguire and T. Naicker, Magn. Res. Chem., 2008, 46, 1089-1095.
12. S. Orlandi, M. Benaglia, G. Dell'Anna and G. Celentano, J. Organomet. Chem., 2007, 692, 2120-2124.
13. M.H. Chisholm, S.S. Iyer and W.E. Streib, New J. Chem., 2000, 24, 393-398.
14. H.A. McManus and P.J. Guiry, J. Org. Chem., 2002, 67, 8566-8573.
15. S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada and D.P. Curran, J. Am. Chem. Soc., 1998, 120, 3074-3088.
16. Y.T. Jiang, Q.Z. Jiang and X.M. Zhang, J. Am. Chem. Soc., 1998, 120, 3817-3818.
17. H. Nishiyama, Y. Itoh, H. Matsumoto, S.B. Park and K. Itoh, J. Am. Chem. Soc., 1994, 116, 2223-2224.
18. T. Govender, H.K. Hariprakasha, H.G. Kruger and A.P. Marchand, Tetrahedron-Asymmetry, 2003, 14, 1553-1557.
19. A.P. Marchand, Z.L. Huang, Z.B. Chen, H.K. Hariprakasha, I.N.N. Namboothiri, J.S. Brodbelt and M.L. Reyzer, J. Heterocyc. Chem., 2001, 38, 1361-1368.
20. S. Kaden and H.U. Reissig, Organic Lett., 2006, 8, 4763-4766.
21. N. Sewald and H.-D. Jakubke, Peptides: Chemistry and Biology, Wiley-VCH Verlag Gmbh, Weinheim, Germany, Reprint 2005.
22. D.A. Evans, K.A. Woerpel, M.M. Hinman and M.M. Faul, J.Am. Chem. Soc., 1991, 113, 726-728.
23. G. Desimoni, G. Faita and P.P. Righetti, Tetrahedron Lett., 1996, 37, 3027-3030.
24. P.G. Cozzi, P. Orioli, E. Tagliavini and A. Umani-Ronchi, Tetrahedron Lett., 1997, 38, 145-148.
25. S. Crosignani, G. Desimoni, G. Faita and P. Righetti, Tetrahedron, 1998, 54, 15721-15730.
26. E.J. Corey, N. Imai and H.Y. Zhang, J. Am. Chem. Soc., 1991, 113, 728-729.
27. D.A. Evans, S.J. Miller, T. Lectka and P. von Matt, J. Am. Chem. Soc., 1999, 121, 7559-7573.
28. D.A. Evans, M.C. Kozlowski and J.S. Tedrow, Tetrahedron Lett., 1996, 37, 7481-7484.
29. D.A. Evans, S.J. Miller and T. Lectka, J. Am. Chem. Soc., 1993, 115, 6460-6461.
30. I. Atodiresei, I. Schiffers and C. Bolm, Tetrahedron-Asymmetry, 2006, 17, 620-633.
31. J.M. Takacs, E.C. Lawson, M.J. Reno, M.A. Youngman and D.A. Quincy, Tetrahedron-Asymmetry, 1997, 8, 3073-3078.
32. E.J. Corey and K. Ishihara, Tetrahedron Lett, 1992, 33, 6807-6810.
33. G. Desimoni, G. Faita, A.G. Invernizzi and P. Righetti, Tetrahedron, 1997, 53, 7671-7688.
34. P. Carbone, G. Desimoni, G. Faita, S. Filippone and P. Righetti, Tetrahedron, 1998, 54, 6099-6110.
35. D.M. Du, Z.Y. Wang, D.C. Xu and W.T. Hua, Synthesis, 2002, 2347-2352.
36. M. Gomez, S. Jansat, G. Muller, M.A. Maestro and J. Mahia, Organometallics, 2002, 21, 1077-1087.
37. N. Cabedo, I. Andreu, M.C.R. de Arellano, A. Chagraoui, A. Serrano, A. Bermejo, P. Protais and D. Cortes, J. Med. Chem., 2001, 44, 1794-1801.
38. D.A. Evans, D.M. Barnes, J.S. Johnson, T. Lectka, P. von Matt, S.J. Miller, J.A. Murry, R.D. Norcross, E.A. Shaughnessy and K.R. Campos, J. Am. Chem. Soc., 1999, 121, 7582-7594.
39. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, USA, 2004.