D-Isomannide in synthesis: Asymmetric Diels-Alder reactions with novel homochiral bis-imine Cu2+-catalysts

Tetrahedron Asymmetry

Volumn 13, Issue 15, 2002, Pages 1673-1679

  De Coster, Gert ^a   Vandyck, Koen ^a   Van der Eycken, Erik ^a   Van der Eycken, Johan ^a   Elseviers, Myriam ^b   Röper, Harald ^b  

^a GHENT UNIVERSITY   (Belgium)

^b Eridania Béghin Say RandD ^*  (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER ION; CYCLOPENTADIENE DERIVATIVE; DEXTRO ISOMANNIDE; IMIDE; IMINE; N (PHENYLMETHYLIDENE) N 6 [[(PHENYLMETHYLIDENE)AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N [(2 CHLORO 6 FLUOROPHENYL)METHYLIDENE] N 6 [[[(2 CHLORO 6 FLUOROPHENYL)METHYLIDENE]AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N [(2 CHLORO 6 NITROPHENYL)METHYLIDENE] N 6 [[[(2 CHLORO 6 NITROPHENYL)METHYLIDENE]AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N [(2,3,4,5,6 PENTAFLUOROPHENYL)METHYLIDENE] N 6 [[[(2,3,4,5,6 PENTAFLUOROPHENYL)METHYLIDENE]AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N [(2,6 DICHLOROPHENYL)METHYLIDENE] N 6 [[[(2,6 DICHLOROPHENYL)METHYLIDENE]AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N [(4 METHOXYPHENYL)METHYLIDENE] N 6 [[[(4 METHOXYPHENYL)METHYLIDENE]AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N [[2 HYDROXY 3,5 DI(TERT BUTYL)PHENYL]METHYLIDENE] N 6 [[[[2 HYDROXY 3,5 DI(TERT BUTYL)PHENYL]METHYLIDENE]AMINO]HEXAHYDROFURO[3,2 B]FURAN 3 YL]AMINE; N TERT CROTONOYLOXAZOLIDINONE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DIELS ALDER REACTION; PRIORITY JOURNAL;

EID: 0037077801     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00411-1     Document Type: Article

References (29)

1. Fauconnier A. C. R. Acad. Sci. 95:1882;991.
2. Fauconnier A. Bull. Soc. Chim. Fr. 41:1884;119.
3. Hockett R.C., Fletcher H.G. Jr., Sheffield E.L., Goepp R.M. Jr., Soltzberg S. J. Am. Chem. Soc. 68:1946;930.
4. Wiggins L.F. J. Chem. Soc. 1945;4.
5. Wiggins L.F., Montgomery R. Nature. 157:1946;372.
6. Montgomery R., Wiggins L.F. J. Am. Chem. Soc. 68:1946;390.
7. Cerè V., Mazzini C., Paolucci C., Pollicino S., Fava A. J. Org. Chem. 58:1993;4567-4571.
8. Ejjiyar S., Saluzzo C., Amouroux R., Massoui M. Tetrahedron Lett. 38:1997;1575-1576.
9. Chao Q., Zhang J., Pickering L., Jahnke T.S., Nair V. Tetrahedron. 54:1998;3113-3124.
10. Bakos J., Heil B., Markó L. J. Organomet. Chem. 253:1983;249-252.
11. Tamion R., Marsais F., Ribereau P., Quéguinier G., Abenhaim D., Loupy A., Munnier L. Tetrahedron: Asymmetry. 4:1993;1879-1890.
12. Tamion R., Marsais F., Ribereau P., Quéguinier G. Tetrahedron: Asymmetry. 4:1993;2415-2418.
13. Loupy A., Monteux D.A. Tetrahedron. 58:2002;1541-1549.
14. Loupy A., Monteux D.A. Tetrahedron Lett. 37:1996;7023-7026.
15. Jones G.B., Guzel M. Tetrahedron Lett. 41:2000;4695-4699.
16. Hashimoto S., Komeshima N., Koga K. J. Chem. Soc., Chem. Commun. 1979;437-438.
17. For reviews, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066; (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019; (d) Narasaka, K. Synthesis 1991, 1-11; (e) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, pp. 315-399.
18. For reviews, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066; (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019; (d) Narasaka, K. Synthesis 1991, 1-11; (e) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, pp. 315-399.
19. For reviews, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066; (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019; (d) Narasaka, K. Synthesis 1991, 1-11; (e) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, pp. 315-399.
20. For reviews, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066; (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019; (d) Narasaka, K. Synthesis 1991, 1-11; (e) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, pp. 315-399.
21. For reviews, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92; (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066; (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019; (d) Narasaka, K. Synthesis 1991, 1-11; (e) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 5, pp. 315-399.
22. Evans D.A., Miller S.J., Lectka T., von Matt P. J. Am. Chem. Soc. 121:1999;7559-7573.
23. Evans D.A., Barnes D.M., Johnson J.S., Lectka T., von Matt P., Miller S.J., Murry J.A., Norcross R.D., Shaughnessy E.A., Campos K.R. J. Am. Chem. Soc. 121:1999;7582-7594.
24. Mitsunobu O. Synthesis. 1981;1-28.
25. Thiem J., Bachmann F. Makromol. Chem. 192:1991;2163-2182.
26. Evans D.A., Miller S.J., Lectka T. J. Am. Chem. Soc. 115:1993;6460-6461. (supplementary material).
27. Evans D.A., Murry J.A., von Matt P., Norcross R.D., Miller S.J. Angew. Chem. Int. Ed. Engl. 34:1995;798-800.
28. Takacs J.M., Lawson E.C., Reno M.J., Youngman M.A., Quincy D.A. Tetrahedron: Asymmetry. 8:1997;3073-3078. and references cited therein.
29. Ghosh A.K., Mathivanan P., Cappiello J. Tetrahedron Lett. 37:1996;3815-3818. and references cited therein.