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Volumn 61, Issue 23, 1996, Pages 8321-8324

Asymmetric Diels-Alder reaction of methacrolein with cyclopentadiene using polymer-supported catalysts: Design of highly enantioselective polymeric catalysts

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Indexed keywords


EID: 0442266988     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960518e     Document Type: Article
Times cited : (101)

References (23)
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    • Salamone, J. C., Ed.; CRC Press: Boca Raton, FL
    • Reviews on polymer-supported reagents and catalysts: (a) Itsuno, S. In Macromolecules 1992: Kahovec, J., Ed.; VSP: Utrecht, 1993; p 413. (b) Itsuno, S. In Polymeric Materials Encyclopedia; Synthesis, Properties and Applications; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; Vol. 10, p 8078. (c) Sherrington D. C.; Hodge, P., Eds. Syntheses and Separations Using Functional Polymers; Wiley: Chichester, 1988. (d) Blossey, E. C.; Ford, W. T. in Comprehensive Polymer Science; Allen, G. Ed.; Pergamon Press: Oxford, 1989; Vol. 6, 81.
    • (1996) Polymeric Materials Encyclopedia; Synthesis, Properties and Applications , vol.10 , pp. 8078
    • Itsuno, S.1
  • 3
    • 0003991951 scopus 로고
    • Wiley: Chichester
    • Reviews on polymer-supported reagents and catalysts: (a) Itsuno, S. In Macromolecules 1992: Kahovec, J., Ed.; VSP: Utrecht, 1993; p 413. (b) Itsuno, S. In Polymeric Materials Encyclopedia; Synthesis, Properties and Applications; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; Vol. 10, p 8078. (c) Sherrington D. C.; Hodge, P., Eds. Syntheses and Separations Using Functional Polymers; Wiley: Chichester, 1988. (d) Blossey, E. C.; Ford, W. T. in Comprehensive Polymer Science; Allen, G. Ed.; Pergamon Press: Oxford, 1989; Vol. 6, 81.
    • (1988) Syntheses and Separations Using Functional Polymers
    • Sherrington, D.C.1    Hodge, P.2
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    • 0001936888 scopus 로고
    • Allen, G. Ed.; Pergamon Press: Oxford
    • Reviews on polymer-supported reagents and catalysts: (a) Itsuno, S. In Macromolecules 1992: Kahovec, J., Ed.; VSP: Utrecht, 1993; p 413. (b) Itsuno, S. In Polymeric Materials Encyclopedia; Synthesis, Properties and Applications; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; Vol. 10, p 8078. (c) Sherrington D. C.; Hodge, P., Eds. Syntheses and Separations Using Functional Polymers; Wiley: Chichester, 1988. (d) Blossey, E. C.; Ford, W. T. in Comprehensive Polymer Science; Allen, G. Ed.; Pergamon Press: Oxford, 1989; Vol. 6, 81.
    • (1989) Comprehensive Polymer Science , vol.6 , pp. 81
    • Blossey, E.C.1    Ford, W.T.2
  • 5
    • 0003905731 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • Reviews on asymmetric Diels-Alder reactions: (a) Paquette, L. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3B. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleminng, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
    • (1984) Asymmetric Synthesis , vol.3 B
    • Paquette, L.A.1
  • 6
    • 0000048258 scopus 로고
    • Trost, B. M., Fleminng, I., Eds.; Pergamon Press: Oxford
    • Reviews on asymmetric Diels-Alder reactions: (a) Paquette, L. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3B. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleminng, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 315
    • Oppolzer, W.1
  • 7
    • 4244033876 scopus 로고
    • Reviews on asymmetric Diels-Alder reactions: (a) Paquette, L. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3B. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleminng, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. (c) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
    • (1992) Chem. Rev. , vol.92 , pp. 1007
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    • (1991) Trends in Organic Chemistry , vol.1 , pp. 199
    • Itsuno, S.1    Ito, K.2
  • 17
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    • note
    • No destruction was observed after 1 week stirring at 200 rpm using a magnetic stirring bar, while polymers cross-linked with divinylbenzene (2) began to lose their spherical shape after 4 days of stirring.
  • 20
    • 85033847104 scopus 로고    scopus 로고
    • note
    • Destruction of the polymeric beads by vigorous stirring results in the formation of fine powder of the polymers, which drastically hinders their handling in filtration and reduces their ability to be recycled repeatedly.


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