메뉴 건너뛰기




Volumn 40, Issue 44, 1999, Pages 7831-7834

Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media

Author keywords

Aqueous media; Aza Diels Alder reaction; Bronsted acid; Danishefsky's diene; Imines

Indexed keywords

ALDEHYDE; ALKADIENE; AMINE; IMINE; INORGANIC ACID; PYRIDONE DERIVATIVE;

EID: 0033615750     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01630-5     Document Type: Article
Times cited : (91)

References (28)
  • 2
    • 0000677232 scopus 로고
    • (b) Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
    • (1993) Chem. Rev. , vol.93 , pp. 2023-2035
    • Li, C.-J.1
  • 5
    • 0029975056 scopus 로고    scopus 로고
    • (e) Li, C.-J. Tetrahedron 1996, 52, 5643-5668.
    • (1996) Tetrahedron , vol.52 , pp. 5643-5668
    • Li, C.-J.1
  • 6
    • 0004216181 scopus 로고    scopus 로고
    • Blackie Academic & Professional: London
    • (f) Organic Reactions in Water; Grieco, P., Ed.; Blackie Academic & Professional: London, 1998.
    • (1998) Organic Reactions in Water
    • Grieco, P.1
  • 7
    • 0032799972 scopus 로고    scopus 로고
    • 2. Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1045-1048. Akiyama, T.; Takaya, J.; Kagoshima, H. Chem. Lett. 1999, 947-948.
    • (1999) Synlett , pp. 1045-1048
    • Akiyama, T.1    Takaya, J.2    Kagoshima, H.3
  • 10
    • 0032850169 scopus 로고    scopus 로고
    • 4. Kobayashi and co-workers recently found Mannich-type reaction in water promoted by means of Brønsted acids-surfactant combined catalyst. See: Manabe, K.; Mori, Y.; Kobayashi, S. Synlett 1999, 1401-1402.
    • (1999) Synlett , pp. 1401-1402
    • Manabe, K.1    Mori, Y.2    Kobayashi, S.3
  • 12
    • 0000730407 scopus 로고
    • Comprehensive organic synthesis
    • Trost, B. M.; Fleming, I. Eds. Pergamon Press: Oxford
    • 6. Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds. Hetero dienophile additions to dienes. Pergamon Press: Oxford, 1991; Vol. 5, p 401. Waldmann, H. Synthesis 1994, 535-551.
    • (1991) Hetero Dienophile Additions to Dienes , vol.5 , pp. 401
    • Weinreb, S.M.1
  • 13
    • 0028264476 scopus 로고
    • 6. Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds. Hetero dienophile additions to dienes. Pergamon Press: Oxford, 1991; Vol. 5, p 401. Waldmann, H. Synthesis 1994, 535-551.
    • (1994) Synthesis , pp. 535-551
    • Waldmann, H.1
  • 18
    • 0000656506 scopus 로고
    • 8. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 979-981. Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3121-3124. Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10520-10524
    • Ishihara, K.1    Miyata, M.2    Hattori, K.3    Tada, T.4    Yamamoto, H.5
  • 19
    • 0031980938 scopus 로고    scopus 로고
    • 8. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 979-981. Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3121-3124. Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 979-981
    • Kobayashi, S.1    Komiyama, S.2    Ishitani, H.3
  • 20
    • 0032484179 scopus 로고    scopus 로고
    • 8. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 979-981. Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3121-3124. Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 3121-3124
    • Yao, S.1    Johannsen, M.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 21
    • 0033546377 scopus 로고    scopus 로고
    • 8. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524. Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 979-981. Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3121-3124. Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221.
    • (1999) J. Org. Chem. , vol.64 , pp. 4220-4221
    • Kobayashi, S.1    Kusakabe, K.2    Komiyama, S.3    Ishitani, H.4
  • 22
    • 0033166293 scopus 로고    scopus 로고
    • 9. For an example of the three component synthesis, see: Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. Ali, T.; Chauham, K. K.; Frost, C. G. Tetrahedron Lett. 1999, 40, 5621-5624.
    • (1995) Chem. Lett. , pp. 423-424
    • Kobayashi, S.1    Ishitani, H.2    Nagayama, S.3
  • 23
    • 0033166293 scopus 로고    scopus 로고
    • 9. For an example of the three component synthesis, see: Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423-424. Ali, T.; Chauham, K. K.; Frost, C. G. Tetrahedron Lett. 1999, 40, 5621-5624.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5621-5624
    • Ali, T.1    Chauham, K.K.2    Frost, C.G.3
  • 24
    • 33845378798 scopus 로고
    • 10. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768-1771. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325-3330.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1768-1771
    • Grieco, P.A.1    Larsen, S.D.2
  • 25
    • 0023802576 scopus 로고
    • 10. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768-1771. Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325-3330.
    • (1988) J. Org. Chem. , vol.53 , pp. 3325-3330
    • Grieco, P.A.1    Parker, D.T.2
  • 26
    • 0004252595 scopus 로고    scopus 로고
    • Organic synthesis in water
    • Grieco, P. A. Ed. Blackie Academic & Professional: London
    • 11. Although three component aza Diels-Alder reaction using cyclopentadiene as a diene have been studied, highly reactive aldehydes such as formaldehyde and glyoxylate were used, see: Parker, D. T. In Organic Synthesis in Water, Grieco, P. A. Ed. Hetero Diels-Alder reactions. Blackie Academic & Professional: London, 1998; pp. 47-81. Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037-3040.
    • (1998) Hetero Diels-Alder Reactions , pp. 47-81
    • Parker, D.T.1
  • 27
    • 0001153217 scopus 로고
    • 11. Although three component aza Diels-Alder reaction using cyclopentadiene as a diene have been studied, highly reactive aldehydes such as formaldehyde and glyoxylate were used, see: Parker, D. T. In Organic Synthesis in Water, Grieco, P. A. Ed. Hetero Diels-Alder reactions. Blackie Academic & Professional: London, 1998; pp. 47-81. Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037-3040.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3037-3040
    • Sisko, J.1    Weinreb, S.M.2
  • 28
    • 0001648506 scopus 로고    scopus 로고
    • 12. Chiral Lewis-acid catalyzed enantioselective Diels-Alder reaction with cyclopentadiene has been reported. Otto, S.; Boccaletti, G.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1998, 120, 4238-4239.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4238-4239
    • Otto, S.1    Boccaletti, G.2    Engberts, J.B.F.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.