A novel polymer-supported scandium catalyst which shows high activity in water

Angewandte Chemie - International Edition

Volumn 39, Issue 3, 2000, Pages 567-569

  Nagayama, Satoshi ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldol reactions; Catalysts; Lewis acids; Polymers; Scandium

Indexed keywords

POLYMER; SCANDIUM;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; THERMODYNAMICS;

EID: 0034602986     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000204)39:3<567::AID-ANIE567>3.0.CO;2-G     Document Type: Article

References (33)

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11. While most Lewis acids were believed to be unstable in water, water-tolerant Lewis acids are now known; a) S. Kobayashi, Chem. Lett. 1991, 2187-2190; b) S. Kobayashi, S. Nagayama, T. Busujima, J. Am. Chem. Soc. 1998, 120, 8287-8288; c) J. B. F. N. Engberts, B. L. Feringa, E. Keller, S. Otto, Recl. Trav. Chim. Pays-Bas 1996, 115, 457-446. See also Ref. [2].
12. While most Lewis acids were believed to be unstable in water, water- tolerant Lewis acids are now known; a) S. Kobayashi, Chem. Lett. 1991, 2187-2190; b) S. Kobayashi, S. Nagayama, T. Busujima, J. Am. Chem. Soc. 1998, 120, 8287-8288; c) J. B. F. N. Engberts, B. L. Feringa, E. Keller, S. Otto, Recl. Trav. Chim. Pays-Bas 1996, 115, 457-446. See also Ref. [2].
13. While most Lewis acids were believed to be unstable in water, water- tolerant Lewis acids are now known; a) S. Kobayashi, Chem. Lett. 1991, 2187-2190; b) S. Kobayashi, S. Nagayama, T. Busujima, J. Am. Chem. Soc. 1998, 120, 8287-8288; c) J. B. F. N. Engberts, B. L. Feringa, E. Keller, S. Otto, Recl. Trav. Chim. Pays-Bas 1996, 115, 457-446. See also Ref. [2].
14. For leading references on polymer catalysts, see: a) S. J. Shuttleworth, P. K. Sharma, Synthesis 1997, 1217-1239; b) D. C. Bailey, S. H. Langer, Chem. Rev. 1981, 81, 109-148; A. Akelah, D. C. Sherrington, Chem. Rev. 1981, 81, 557-587; d) J. M. J. Frechet, Tetrahedron 1981, 37, 663-683. For recent works, see: e) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154. and references therein.
15. For leading references on polymer catalysts, see: a) S. J. Shuttleworth, P. K. Sharma, Synthesis 1997, 1217-1239; b) D. C. Bailey, S. H. Langer, Chem. Rev. 1981, 81, 109-148; A. Akelah, D. C. Sherrington, Chem. Rev. 1981, 81, 557-587; d) J. M. J. Frechet, Tetrahedron 1981, 37, 663-683. For recent works, see: e) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154. and references therein.
16. For leading references on polymer catalysts, see: a) S. J. Shuttleworth, P. K. Sharma, Synthesis 1997, 1217-1239; b) D. C. Bailey, S. H. Langer, Chem. Rev. 1981, 81, 109-148; A. Akelah, D. C. Sherrington, Chem. Rev. 1981, 81, 557-587; d) J. M. J. Frechet, Tetrahedron 1981, 37, 663-683. For recent works, see: e) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154. and references therein.
17. For leading references on polymer catalysts, see: a) S. J. Shuttleworth, P. K. Sharma, Synthesis 1997, 1217-1239; b) D. C. Bailey, S. H. Langer, Chem. Rev. 1981, 81, 109-148; A. Akelah, D. C. Sherrington, Chem. Rev. 1981, 81, 557-587; d) J. M. J. Frechet, Tetrahedron 1981, 37, 663-683. For recent works, see: e) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154. and references therein.
18. For leading references on polymer catalysts, see: a) S. J. Shuttleworth, P. K. Sharma, Synthesis 1997, 1217-1239; b) D. C. Bailey, S. H. Langer, Chem. Rev. 1981, 81, 109-148; A. Akelah, D. C. Sherrington, Chem. Rev. 1981, 81, 557-587; d) J. M. J. Frechet, Tetrahedron 1981, 37, 663-683. For recent works, see: e) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154. and references therein.
19. Details are described in Supporting Information.
20. While we have previously developed polymer-supported scandium catalysts, most of them work well in organic solvents but reactions proceed sluggishly in water without organic co-solvents. a) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256-2257; b) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1996, 118, 8977-8978; c) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1998, 120, 2985-2986.
21. While we have previously developed polymer-supported scandium catalysts, most of them work well in organic solvents but reactions proceed sluggishly in water without organic co-solvents. a) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256-2257; b) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1996, 118, 8977-8978; c) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1998, 120, 2985-2986.
22. While we have previously developed polymer-supported scandium catalysts, most of them work well in organic solvents but reactions proceed sluggishly in water without organic co-solvents. a) S. Kobayashi, S. Nagayama, J. Org. Chem. 1996, 61, 2256-2257; b) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1996, 118, 8977-8978; c) S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1998, 120, 2985-2986.
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27. [17] the degree of sulfonation of 5 was determined hy titration. The scandium loading of 1 was determined by elemental analysis. All details are given in the Supporting Information.
28. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
29. No reaction occurred without 1. The reaction proceeded in lower yield using a polymer-supported scandium catalyst without the spacer moiety.
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