Poly(Ethylene Glycol)-Supported Proline: A Versatile Catalyst for the Enantioselective Aldol and Iminoaldol Reactions

Advanced Synthesis and Catalysis

Volumn 344, Issue 5, 2002, Pages 533-542

  Benaglia, Maurizio ^a   Cinquini, Mauro ^a   Cozzi, Franco ^a   Puglisi, Alessandra ^a   Celentano, Giuseppe ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Aldol reactions; Asymmetric catalysis; Iminoaldol reactions; Soluble polymers; Supported catalysis

Indexed keywords

EID: 0001682147     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200207)344:5<533::AID-ADSC533>3.0.CO;2-Y     Document Type: Article

References (44)

1. a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
2. b) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621;
3. c) P. A. Grieco, N. Fukamiya, M. Miyashita, J. Chem. Soc. Chem. Commun. 1976, 573-575.
4. For discussions on the reaction mechanism see: d) C. Agami, Bull. Chem. Soc.Fr. 1988, 3, 499-507; e) D. Rajagopal, M. S. Moni, S. Subramanian, S. Swaminathan, Tetrahedron Asymmetry 1999, 10, 1631-1634.
5. For discussions on the reaction mechanism see: d) C. Agami, Bull. Chem. Soc.Fr. 1988, 3, 499-507; e) D. Rajagopal, M. S. Moni, S. Subramanian, S. Swaminathan, Tetrahedron Asymmetry 1999, 10, 1631-1634.
6. For recent applications to aldol and related reactions see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; c) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; d) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575; e) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
7. For recent applications to aldol and related reactions see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; c) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; d) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575; e) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
8. For recent applications to aldol and related reactions see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; c) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; d) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575; e) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
9. For recent applications to aldol and related reactions see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; c) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; d) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575; e) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
10. For recent applications to aldol and related reactions see: a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; c) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; d) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575; e) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
11. For recent applications to iminoaldol reactions see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337; b) W. Notz, K. Sakthivel, T. Bui, G. Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199-201.
12. For recent applications to iminoaldol reactions see: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337; b) W. Notz, K. Sakthivel, T. Bui, G. Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199-201.
13. For recent applications to conjugated addition reactions see: a) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520-3530; b) M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shraishi, M. Hirama, Tetrahedron 1997, 53, 11223-11236; c) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978; d) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425.
14. For recent applications to conjugated addition reactions see: a) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520-3530; b) M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shraishi, M. Hirama, Tetrahedron 1997, 53, 11223-11236; c) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978; d) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425.
15. For recent applications to conjugated addition reactions see: a) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520-3530; b) M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shraishi, M. Hirama, Tetrahedron 1997, 53, 11223-11236; c) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978; d) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425.
16. For recent applications to conjugated addition reactions see: a) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 61, 3520-3530; b) M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shraishi, M. Hirama, Tetrahedron 1997, 53, 11223-11236; c) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978; d) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425.
17. C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. Int. Ed. Engl. 1995, 34, 412-432.
18. For recent reviews see: a) E. M. Carreira, in Comprehensive Asymmetric Catalysis, Vol. 3, chapter 29.1, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer-Verlag, Heidelberg, 1999; b) S. G. Nelson, Tetrahedron Asymmetry 1998, 9, 357-389.
19. For recent reviews see: a) E. M. Carreira, in Comprehensive Asymmetric Catalysis, Vol. 3, chapter 29.1, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer-Verlag, Heidelberg, 1999; b) S. G. Nelson, Tetrahedron Asymmetry 1998, 9, 357-389.
20. For leading references to chiral Lewis-base catalyzed enantioselective aldol reactions see: S. E. Denmark, R. A. Stavenger, J. Am. Chem. Soc. 2000, 122, 8837-8847 and references cited therein.
21. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, M. Pitillo, J. Org. Chem. 2001, 66, 3160-3166.
22. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739.
23. For an excellent review on the immobilization of ligands and catalysts on polymer supports, see: a) Chiral Catalyst Immobilization and Recycling, (Eds.: D. E. De Vos, I. F. J. Vankelecom, P.A. Jacobs), Wiley-VCH, Weinheim, 2000; for reports concerning the use of PEG as support in this context see: b) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; c) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; d) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048.
24. For an excellent review on the immobilization of ligands and catalysts on polymer supports, see: a) Chiral Catalyst Immobilization and Recycling, (Eds.: D. E. De Vos, I. F. J. Vankelecom, P.A. Jacobs), Wiley-VCH, Weinheim, 2000; for reports concerning the use of PEG as support in this context see: b) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; c) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; d) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048.
25. For an excellent review on the immobilization of ligands and catalysts on polymer supports, see: a) Chiral Catalyst Immobilization and Recycling, (Eds.: D. E. De Vos, I. F. J. Vankelecom, P.A. Jacobs), Wiley-VCH, Weinheim, 2000; for reports concerning the use of PEG as support in this context see: b) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; c) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; d) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048.
26. For an excellent review on the immobilization of ligands and catalysts on polymer supports, see: a) Chiral Catalyst Immobilization and Recycling, (Eds.: D. E. De Vos, I. F. J. Vankelecom, P.A. Jacobs), Wiley-VCH, Weinheim, 2000; for reports concerning the use of PEG as support in this context see: b) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; c) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; d) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048.
27. For an excellent review on asymmetric organic catalysis see: P. I. Dalko, L. Moisan Angew. Chem. Int. Ed. Engl. 2001, 40, 3726-3748.
28. D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489-509.
29. [8]) and insoluble polystyrene-supported-bisoxazolines/Cu(II) complexes, see: S. Orlandi, A. Mandoli, D. Pini, P. Salvadori, Angew. Chem. Int. Ed. 2001, 40, 2519-2521, showed considerable decrease of catalytic efficiency upon recovery and recycling.
30. Obviously, PEG cannot be expected to exert the stereo-directing effect of a peptide chain.
31. For a preliminary account of the part of this work concerning the PEG-Pro-catalyzed aldol condensation, see: M. Benaglia, G. Celentano, F. Cozzi, Adv. Synth. Catal. 2001, 343, 171-173.
32. w PEG, see: a) M. Benaglia, R. Annunziata, M. Cinquini, F. Cozzi, S. Ressel, J. Org. Chem. 1998, 63, 8628-8629; b) N. N. Reed, K. D. Janda, Org. Lett. 2000, 2, 1311-1313.
33. w PEG, see: a) M. Benaglia, R. Annunziata, M. Cinquini, F. Cozzi, S. Ressel, J. Org. Chem. 1998, 63, 8628-8629; b) N. N. Reed, K. D. Janda, Org. Lett. 2000, 2, 1311-1313.
34. The highly hygroscopic nature of PEG can be one of the factors that account for this behavior. In this hypothesis, the observed lower yields could arise from the fact that a wet sample (and thus a lesser amount) of catalyst was actually recycled. Other hypotheses, such as hydrolysis of the ester linkages and/or degradation of the polymer backbone were ruled out by checking by NMR the integrity of the recovered catalyst. A precise evaluation of the water content of the catalyst by NMR was not possible.
35. A. Fujii, M. Sodeoka, Tetrahedron Lett. 1999, 40, 8011-8014.
36. For an example of the use of polymer supported catalysts in the asymmetric Strecker reaction, see: M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902.
37. Pre-formed aliphatic aldimines were not employed in the iminoaldol reaction because of their intrinsic instability.
38. Review: D. J. Berrisford, C. Bolm, K.B. Sharpless, Angew. Chem. Int. Ed. Engl. 1995, 54, 1059-1070.
39. Review: P. O'Brien, Angew. Chem. Int. Ed. Engl. 1999, 38, 326-329.
40. P. J. Wash, K. B. Sharpless, Synlett 1993, 605-606.
41. [2b,2e]).
42. [2b]) has reported that the three-component reaction between hydroxyacetone, 2-methylpropanal, and 4-methoxyaniline afforded (57% yield) a 17:1 mixture of syn and anti isomers, the syn isomer having a 65% ee and the same configuration indicated for adducts 14 and 15. Attempts to use catalyst 2 in this reaction led to the products in very low yields (10-15%).
43. a) E. Wada, J. Funakoshi, S. Kanemasa, Bull. Chem. Soc. Jpn. 1992, 65, 2456-2464;
44. b) G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky, C. F. Barbas, III, J. Am. Chem. Soc. 1997, 119, 8131-8132.