Enantioselective Aldol Condensations Catalyzed by Poly(ethylene glycol)-Supported Proline

Advanced Synthesis and Catalysis

Volumn 343, Issue 2, 2001, Pages 171-173

  Benaglia, Maurizio ^a   Celentano, Giuseppe ^a   Cozzi, Franco ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Aldol reactions; Asymmetric catalysis; Catalyst immobilization; Chiral bases; Soluble polymers

Indexed keywords

EID: 0000776283     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010226)343:2<171::AID-ADSC171>3.0.CO;2-3     Document Type: Review

References (24)

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2. nd ed., (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
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10. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, Org. Lett. 2000, 2, 1737-1739.
11. These intermolecular aldol condensations catalyzed by proline and proline derivatives have recently been described: (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; for examples of proline-catalyzed intramolecular aldol-type processes see: (c) U. Eder, G. Sauer, R. Weichert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497; (d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; (e) T. Bui, C. F. Barbas, III, Tetrahedron Lett. 2000, 41, 6951-6954.
12. These intermolecular aldol condensations catalyzed by proline and proline derivatives have recently been described: (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; for examples of proline-catalyzed intramolecular aldol-type processes see: (c) U. Eder, G. Sauer, R. Weichert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497; (d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; (e) T. Bui, C. F. Barbas, III, Tetrahedron Lett. 2000, 41, 6951-6954.
13. These intermolecular aldol condensations catalyzed by proline and proline derivatives have recently been described: (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; for examples of proline-catalyzed intramolecular aldol-type processes see: (c) U. Eder, G. Sauer, R. Weichert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497; (d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; (e) T. Bui, C. F. Barbas, III, Tetrahedron Lett. 2000, 41, 6951-6954.
14. These intermolecular aldol condensations catalyzed by proline and proline derivatives have recently been described: (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; for examples of proline-catalyzed intramolecular aldol-type processes see: (c) U. Eder, G. Sauer, R. Weichert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497; (d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; (e) T. Bui, C. F. Barbas, III, Tetrahedron Lett. 2000, 41, 6951-6954.
15. These intermolecular aldol condensations catalyzed by proline and proline derivatives have recently been described: (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; for examples of proline-catalyzed intramolecular aldol-type processes see: (c) U. Eder, G. Sauer, R. Weichert, Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497; (d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; (e) T. Bui, C. F. Barbas, III, Tetrahedron Lett. 2000, 41, 6951-6954.
16. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
17. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
18. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
19. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
20. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
21. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
22. For the immobilization of chiral ligands on soluble polymers see: (a) C. Bolm, A. Gerlach, Angew. Chem. Int. Ed. Engl. 1997, 36, 741-743; (b) H. Han, K. D. Janda, Angew. Chem. Int. Ed. Engl. 1997, 36, 1731-1733; (c) Q. Fang, C. Ren, C. Yeung, W. Hu, A. S. C. Chan, J. Am. Chem. Soc. 1999, 121, 7407-7408; (d) C. Bolm., C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem. 1999, 64, 5730-5731; (e) T. S. Reger, K. D. Janda, J. Am. Chem. Soc. 2000, 122, 6929-6934; (f) M. Glos, O. Reiser, Org. Lett. 2000, 2, 2045-2048. For the use of fluorous biphase systems as solubility device in this context, see: (g) G. Pozzi, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
23. For a detailed description of the isolation, purification, and yield determination of PEG-supported compounds see: R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, Chem. Eur. J. 2000, 6, 133-138. When 2 was prepared using 4 mol equiv. each of DIC and hydroxyproline in refluxing 1,2-dichloroethane the yield was 40%. 4-Hydroxyproline proved to be optically stable when heated at 150 °C for 20 h.
24. N. Ikeda, K. Omori, H. Yamamoto, Tetrahedron Lett. 1986, 27, 1175-1178.