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Volumn , Issue 11, 2002, Pages 1898-1900

Montmorillonite K10-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimines, generated in situ from aliphatic aldehydes and amine, in aqueous media

Author keywords

Danishefsky's dienes; Diels Alder reactions; Montmorillonite; Schiff bases; Water

Indexed keywords

ALDEHYDE DERIVATIVE; ALKADIENE; AMINE; IMINE; MONTMORILLONITE; PYRIDONE DERIVATIVE;

EID: 0036423241     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34870     Document Type: Article
Times cited : (20)

References (39)
  • 16
    • 0000677232 scopus 로고
    • For reviews of the reaction in aqueous media: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997. (c) Lubineau, A.; Aug, J.; Queneau, Y. Synthesis 1994, 741. (d) Li, C.-J. Tetrahedron 1996, 52, 5643. (e) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998. (f) Modern Solvents in Organic Synthesis (Topics In Current Chemistry, 206); Knochel, P.; Houk, K. N.; Kessler, H., Eds.; Springer Verlag: Berlin, 1999.
    • (1993) Chem. Rev. , vol.93 , pp. 2023
    • Li, C.-J.1
  • 17
    • 0003602022 scopus 로고    scopus 로고
    • John Wiley: New York
    • For reviews of the reaction in aqueous media: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997. (c) Lubineau, A.; Aug, J.; Queneau, Y. Synthesis 1994, 741. (d) Li, C.-J. Tetrahedron 1996, 52, 5643. (e) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998. (f) Modern Solvents in Organic Synthesis (Topics In Current Chemistry, 206); Knochel, P.; Houk, K. N.; Kessler, H., Eds.; Springer Verlag: Berlin, 1999.
    • (1997) Organic Reactions in Aqueous Media
    • Li, C.-J.1    Chan, T.-H.2
  • 18
    • 2542473847 scopus 로고
    • For reviews of the reaction in aqueous media: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997. (c) Lubineau, A.; Aug, J.; Queneau, Y. Synthesis 1994, 741. (d) Li, C.-J. Tetrahedron 1996, 52, 5643. (e) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998. (f) Modern Solvents in Organic Synthesis (Topics In Current Chemistry, 206); Knochel, P.; Houk, K. N.; Kessler, H., Eds.; Springer Verlag: Berlin, 1999.
    • (1994) Synthesis , pp. 741
    • Lubineau, A.1    Aug, J.2    Queneau, Y.3
  • 19
    • 0029975056 scopus 로고    scopus 로고
    • For reviews of the reaction in aqueous media: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997. (c) Lubineau, A.; Aug, J.; Queneau, Y. Synthesis 1994, 741. (d) Li, C.-J. Tetrahedron 1996, 52, 5643. (e) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998. (f) Modern Solvents in Organic Synthesis (Topics In Current Chemistry, 206); Knochel, P.; Houk, K. N.; Kessler, H., Eds.; Springer Verlag: Berlin, 1999.
    • (1996) Tetrahedron , vol.52 , pp. 5643
    • Li, C.-J.1
  • 20
    • 0004216181 scopus 로고    scopus 로고
    • Blackie Academic & Professional: London
    • For reviews of the reaction in aqueous media: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997. (c) Lubineau, A.; Aug, J.; Queneau, Y. Synthesis 1994, 741. (d) Li, C.-J. Tetrahedron 1996, 52, 5643. (e) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998. (f) Modern Solvents in Organic Synthesis (Topics In Current Chemistry, 206); Knochel, P.; Houk, K. N.; Kessler, H., Eds.; Springer Verlag: Berlin, 1999.
    • (1998) Organic Reactions in Water
    • Grieco, P.1
  • 21
    • 0003800720 scopus 로고    scopus 로고
    • Springer Verlag: Berlin
    • For reviews of the reaction in aqueous media: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997. (c) Lubineau, A.; Aug, J.; Queneau, Y. Synthesis 1994, 741. (d) Li, C.-J. Tetrahedron 1996, 52, 5643. (e) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998. (f) Modern Solvents in Organic Synthesis (Topics In Current Chemistry, 206); Knochel, P.; Houk, K. N.; Kessler, H., Eds.; Springer Verlag: Berlin, 1999.
    • (1999) Modern Solvents in Organic Synthesis (Topics In Current Chemistry) , vol.206
    • Knochel, P.1    Houk, K.N.2    Kessler, H.3
  • 29
    • 0011370984 scopus 로고    scopus 로고
    • note
    • 11 yields of the adducts are not excellent.
  • 35
    • 0033609786 scopus 로고    scopus 로고
    • For aldol reaction catalyzed by montmorillonite K10 in water, see: Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 10789.
    • (1999) Tetrahedron , vol.55 , pp. 10789
    • Loh, T.-P.1    Li, X.-R.2
  • 36
    • 0011314468 scopus 로고    scopus 로고
    • note
    • 3N) gave propyl-substituted 2,3-dihydro-4-pyridone (34.6 mg, 0.141 mmol) in 89% yield.
  • 37
    • 0011367032 scopus 로고    scopus 로고
    • note
    • 3CN were carried out at -10°C.
  • 38
    • 0011318831 scopus 로고    scopus 로고
    • note
    • Even when the catalyst loading was reduced to 50 mg/mmol, 10% of the standard procedure shown above, the adducts were obtained in the same yields in the three-component synthesis under the conditions A, B, and C..
  • 39
    • 0035925228 scopus 로고    scopus 로고
    • For water-accelerated organic transformations, see:Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
    • (2001) Chem. Commun. , pp. 299
    • Ribe, S.1    Wipf, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.