Synthesis of perfluoroalkyl-substituted bis(oxazolines) as ligands for catalytic enantioselective reactions

European Journal of Organic Chemistry

Volumn , Issue 7, 2003, Pages 1191-1197

  Annunziata, Rita ^a   Benaglia, Maurizio ^a   Cinquini, Mauro ^a   Cozzi, Franco ^a   Pozzi, Gianluca ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Asymmetric catalysis; Biphasic catalysis; Fluorous ligands; Homogeneous catalysis; Supported catalysis

Indexed keywords

1 [4 [[3,5 BIS(PERFLUOROOCTYL)PHENYL]METHOXY]PHENYL] 2,2 BIS [2 [4 (1,1 DIMETHYLETHYL) 1,3 OXAZOLIN 2 YL]]PROPANE; 1,3 BIS[4 [[3,5 BIS(PERFLUOROOCTYL)PHENYL]METHOXY]PHENYL] 2,2 BIS[4 (1,1 DIMETHYLETHYL) 1,3 OXAZOLIN 2 YL]PROPANE; ALKYL GROUP; FLUORINE; GLYOXYLIC ACID DERIVATIVE; LIGAND; OXAZOLINE DERIVATIVE; PERFLUORO COMPOUND; POLYMER; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CHROMATOGRAPHY; COMBINATORIAL CHEMISTRY; CYCLOPROPANATION; ENANTIOSELECTIVITY; INTERMETHOD COMPARISON; PHASE SEPARATION; RECYCLING; SOLUBILITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037395354     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390173     Document Type: Article

References (61)

1. Review: A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
2. R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, 1994.
3. Chiral Catalyst Immobilization and Recycling (Eds.: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000.
4. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
5. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
6. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
7. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
8. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
9. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
10. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
11. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
12. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
13. [4a] M. I. Burguete, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, C. I. Herrerias, S. V. Luis, J. A. Mayoral, J. Org. Chem. 2001, 66, 8893-8901, and references therein. [4b] D. Rechavi, M. Lemaire, Org. Lett. 2001, 3, 2493-2496. [4c] K. Hallman, C. Moberg, Tetrahedron: Asymmetry 2001, 12, 1475-1478. [4d] J. K. Park, S.-W. Kim, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2001, 12, 2931-2935. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4e] S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521; Angew. Chem. 2001, 113, 2587-2589. [4f] R. J. Clarke, I. J. Shannon, Chem. Commun. 2001, 1936-1937. [4g] A. Corma, H. Garcia, A. Moussaif, A. M. J. Sabater, R. Zniber, A. Redouane, Chem. Commun. 2002, 1058-1059. For the immobilization of box on polymer supports containing dendrimeric cross-linkers see: [4h] M. I. Burguete, E. Diez-Barra, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, R. Gonzalez, C. I. Herrerias, S. V. Luis, J. A. Mayoral, Bioorg. Med. Chem. Lett. 2002, 12, 1821-1824. [4i] D. Rechavi, M. Lemaire, J. Mol. Catal. A: Chem. 2002, 182-183, 239-247.
14. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, M. Pitillo, J. Org. Chem. 2001, 66, 3160-3166.
15. M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048.
16. Review: D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489-509.
17. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
18. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
19. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
20. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
21. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
22. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
23. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
24. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
25. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
26. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
27. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
28. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
29. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
30. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
31. For the immobilizaton of other chiral ligands and catalysts on modified PEG see; [8a] H. Han, K. D. Janda, Tetrahedron Lett. 1997, 38, 1527-1530, and references therein. [8b] C. Bolm, A. Gerlach, Eur J. Org. Chem. 1998, 21-27, and references therein. [8c] T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934. [8d] M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173. [8e] R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686. [8f] Q. H. Fan, G. J. Deng, C. C. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1241-1247. [8g] P. Guerreiro, V. Ratovelomanana-Vidal, J.-P. Genet, P. Dellis, Tetrahedron Lett. 2001, 42, 3423-3426. [8h] Y. Q. Kuang, S. Y. Zhang, L. L. Wei, Tetrahedron Lett. 2001, 42, 5925-5927. [8i] H. Guo, X. Shi, Z. Qiao, S. Hou, M. Wang, Chem. Commun. 2002, 118-119. [8j] M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152. [8k] M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542. For the immobilizaton of achiral ligands and catalysts on modified PEG see: [8l] Q. Yao, Angew. Chem. Int. Ed. 2000, 39, 3896-3898; Angew. Chem. 2000, 112, 4060-4062. [8m] R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739. [8n] M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
32. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
33. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
34. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
35. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
36. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
37. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
38. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
39. Reviews on fluorous biphase chemistry: [9a] I. T. Horvath, Acc. Chem. Res. 1998, 31, 641-650. [9b] L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587-605. [9c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193. [9d] D. P. Curran, Synlett 2001, 1488-1496. Reviews on fluorous biphase catalysis: E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41. [9f] E. G. Hope, A. M. Stuart, J. Fluorine Chem. 1999, 100, 75-83. [9g] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680. For definitions in this field: [9h] J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823-3825.
40. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
41. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
42. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
43. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
44. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
45. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
46. Review on perfluoroalkyl-substituted chiral ligands and catalysts: [10a] G. Pozzi, M. Cavazzini, S. Quici, D. Maillard, D. Sinou, J. Mol. Catal. A: Chem. 2002, 182-183, 455-461. For other examples not included in ref. [10a] see: [10b] M. Cavazzini, S. Quici, G. Pozzi, Tetrahedron 2002, 58, 3943-3949. [10c] Y. Tian, Q. C. Yang, T. C. W. Mak, K. S. Chan, Tetrahedron 2002, 58, 3951-3961. [10d] Y. Nakamura, S. Takeuchi, K. Okumura, Y. Ohgo, D. P. Curran, Tetrahedron 2002, 58, 3963-3969. [10e] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 2002, 58, 3971-3976. [10f] Nakamura, S. Takeuchi, S. Zhang, K. Okumura, Y. Ohgo, Tetrahedron Lett. 2002, 43, 3053-3056. [10g] After acceptance of this paper, a synthesis of fluorous chiral box was published: J. Bayardon, D. Sinou, Tetrahedron Lett. 2003, 44, 1449-1451.
47. The use of a deficiency of 5 greatly simplified the chromatographic purification of box 6, which showed a retention factor very similar to that of the benzyl alcohol derived from 5 upon workup.
48. S. Colonna, N. Gaggero, F. Montanari, G. Pozzi, S. Quici, Eur. J. Org. Chem, 2001, 181-186.
49. D. A. Evans, S. W. Tregay, C. S. Burgey, N. A. Paras, V. I. Vojkovsky, J. Am. Chem. Soc. 2000, 122, 7936-7943.
50. [14a] D. A. Evans, K. A. Woerpel, M. N. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728.
51. See also: [14b] R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6009.
52. 2 marginally different results were observed (60% yield, trans/cis = 70:30, 56% ee: see Entry 5, Table 1).
53. 2] complexes of ligands 6 and 9 were employed to catalyze the Diels-Alder cycloaddition between cyclopentadiene and N-acryloyloxazolidinone, the corresponding cycloadducts were obtained in high yield, excellent endo diastereoselectivity, and low ee.
54. Box featuring gem-dibenzyl substitution at the bridging carbon atom are also known to promote cyclopropanation reactions less stereoselectively than the corresponding gem-dimethyl-substituted ligands (see ref. [4a]).
55. For a discussion on the insulating effects of structurally different spacers in perfluorinated ligands see: I. T. Horvath, G. Kiss, R. A. Cook, J. E. Bond, P. A. Stevens, J. Rabai, E. J. Mozeleski, J. Am. Chem. Soc. 1998, 120, 3133-31453.
56. For a recent discussion on the influence of the substitution pattern at the box-bridging carbon atom on the steric course of box-mediated asymmetric syntheses see: S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878, and references therein.
57. 1-catalyzed cyclopropanation reaction has been recently calculated: J. M. Fraile, J. I. Garcia, V. Martinez-Merino, J. A. Mayoral, L. Salvatella, J. Am. Chem. Soc 2001, 123, 7616-7625, showing that the catalytic complex adopts a trigonal geometry.
58. 1-catalyzed cyclopropanation reaction has been recently calculated: J. M. Fraile, J. I. Garcia, V. Martinez-Merino, J. A. Mayoral, L. Salvatella, J. Am. Chem. Soc 2001, 123, 7616-7625, showing that the catalytic complex adopts a trigonal geometry.
59. 11 promoted reactions see: I. W. Davies, R. J. Deeth, R. D. Larsen, P. J. Reider, Tetrahedron Lett. 1999, 40, 1233-1236.
60. For a similar observation of diazoacetate-derived decomposition products contaminating polymer-supported box ligands see ref. [4h]
61. Preliminary results showed that ligand 9 could also be recovered by filtration through a short (ca. 3 cm) plug of fluorous reverse-phase silica gel prepared according to: S. Kainz, Z. Y. Luo, D. P. Curran, W. Leitner, Synthesis 1998, 1425-1527. While the recovery yield was very high (90%), a fraction of ligand 9 was contaminated by traces of product 10. Improvement of the recovery procedure is currently under investigation.