메뉴 건너뛰기




Volumn 63, Issue 23, 1998, Pages 8380-8389

(Trialkylsilyl)vinylketenes: Synthesis and application as diene components in Diels-Alder cycloadditions

Author keywords

[No Author keywords available]

Indexed keywords

KETENE DERIVATIVE;

EID: 0032514989     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981289u     Document Type: Article
Times cited : (54)

References (57)
  • 1
    • 15644366023 scopus 로고
    • Wiley: New York
    • (a) Tidwell, T. T. Ketenes; Wiley: New York, 1991.
    • (1991) Ketenes
    • Tidwell, T.T.1
  • 10
    • 37049120946 scopus 로고
    • Only a few cases of vinylketenes participating in [4 + 2] cycloadditions have been reported. For examples, see: (a) Day, A. C.; McDonald, A. N.; Anderson, B. F.; Bartczak, T. J.; Hodder, O. J. R. J. Chem. Soc., Chem. Commun. 1973, 247. (b) Berge, J. M.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 2230. (c) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 38, 1397.
    • (1973) J. Chem. Soc., Chem. Commun. , pp. 247
    • Day, A.C.1    McDonald, A.N.2    Anderson, B.F.3    Bartczak, T.J.4    Hodder, O.J.R.5
  • 11
    • 0001315709 scopus 로고
    • Only a few cases of vinylketenes participating in [4 + 2] cycloadditions have been reported. For examples, see: (a) Day, A. C.; McDonald, A. N.; Anderson, B. F.; Bartczak, T. J.; Hodder, O. J. R. J. Chem. Soc., Chem. Commun. 1973, 247. (b) Berge, J. M.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 2230. (c) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 38, 1397.
    • (1982) Helv. Chim. Acta , vol.65 , pp. 2230
    • Berge, J.M.1    Rey, M.2    Dreiding, A.S.3
  • 12
    • 0031584904 scopus 로고    scopus 로고
    • Only a few cases of vinylketenes participating in [4 + 2] cycloadditions have been reported. For examples, see: (a) Day, A. C.; McDonald, A. N.; Anderson, B. F.; Bartczak, T. J.; Hodder, O. J. R. J. Chem. Soc., Chem. Commun. 1973, 247. (b) Berge, J. M.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 2230. (c) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 38, 1397.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1397
    • Collomb, D.1    Doutheau, A.2
  • 13
    • 0041879484 scopus 로고
    • 1-Methoxy-1-(trimethylsiloxy)-1,3-butadienes undergo Diels-Alder reactions in poor yield unless the diene is substituted with additional electron-donating substituents. For example, see: Savard, J.; Brassard, P. Tetrahedron 1984, 40, 3455.
    • (1984) Tetrahedron , vol.40 , pp. 3455
    • Savard, J.1    Brassard, P.2
  • 17
    • 0004069877 scopus 로고
    • Academic Press: New York
    • For reviews of the photo Wolff rearrangement, see: (a) Regitz, M.; Maas, G. Diazo Compounds-Properties and Synthesis; Academic Press: New York, 1986. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998. (c) Zollinger, H. Diazo Chemistry II: Aliphatic, Inorganic, and Organometallic Compounds; VCH: New York, 1995.
    • (1986) Diazo Compounds-Properties and Synthesis
    • Regitz, M.1    Maas, G.2
  • 18
    • 0003394220 scopus 로고    scopus 로고
    • Wiley: New York
    • For reviews of the photo Wolff rearrangement, see: (a) Regitz, M.; Maas, G. Diazo Compounds-Properties and Synthesis; Academic Press: New York, 1986. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998. (c) Zollinger, H. Diazo Chemistry II: Aliphatic, Inorganic, and Organometallic Compounds; VCH: New York, 1995.
    • (1998) Modern Catalytic Methods for Organic Synthesis with Diazo Compounds
    • Doyle, M.P.1    McKervey, M.A.2    Ye, T.3
  • 19
    • 0003986199 scopus 로고
    • VCH: New York
    • For reviews of the photo Wolff rearrangement, see: (a) Regitz, M.; Maas, G. Diazo Compounds-Properties and Synthesis; Academic Press: New York, 1986. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998. (c) Zollinger, H. Diazo Chemistry II: Aliphatic, Inorganic, and Organometallic Compounds; VCH: New York, 1995.
    • (1995) Diazo Chemistry II: Aliphatic, Inorganic, and Organometallic Compounds
    • Zollinger, H.1
  • 20
    • 0026540762 scopus 로고
    • For applications of this aromatic annulation strategy in the total synthesis of natural products, see: (a) Danheiser, R. L.; Casebier, D. S.; Loebach, J. L. Tetrahedron Lett. 1982, 33, 1149. (b) Danheiser, R. L.; Casebier, D. S.; Huboux, A. H. J. Org. Chem. 1994, 59, 4844. (c) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 116, 9471. (d) Danheiser, R. L.; Trova, M. P. Synlett 1995, 573. (e) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
    • (1982) Tetrahedron Lett. , vol.33 , pp. 1149
    • Danheiser, R.L.1    Casebier, D.S.2    Loebach, J.L.3
  • 21
    • 0027953851 scopus 로고
    • For applications of this aromatic annulation strategy in the total synthesis of natural products, see: (a) Danheiser, R. L.; Casebier, D. S.; Loebach, J. L. Tetrahedron Lett. 1982, 33, 1149. (b) Danheiser, R. L.; Casebier, D. S.; Huboux, A. H. J. Org. Chem. 1994, 59, 4844. (c) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 116, 9471. (d) Danheiser, R. L.; Trova, M. P. Synlett 1995, 573. (e) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
    • (1994) J. Org. Chem. , vol.59 , pp. 4844
    • Danheiser, R.L.1    Casebier, D.S.2    Huboux, A.H.3
  • 22
    • 0028114555 scopus 로고
    • For applications of this aromatic annulation strategy in the total synthesis of natural products, see: (a) Danheiser, R. L.; Casebier, D. S.; Loebach, J. L. Tetrahedron Lett. 1982, 33, 1149. (b) Danheiser, R. L.; Casebier, D. S.; Huboux, A. H. J. Org. Chem. 1994, 59, 4844. (c) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 116, 9471. (d) Danheiser, R. L.; Trova, M. P. Synlett 1995, 573. (e) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9471
    • Danheiser, R.L.1    Helgason, A.L.2
  • 23
    • 0002651490 scopus 로고
    • For applications of this aromatic annulation strategy in the total synthesis of natural products, see: (a) Danheiser, R. L.; Casebier, D. S.; Loebach, J. L. Tetrahedron Lett. 1982, 33, 1149. (b) Danheiser, R. L.; Casebier, D. S.; Huboux, A. H. J. Org. Chem. 1994, 59, 4844. (c) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 116, 9471. (d) Danheiser, R. L.; Trova, M. P. Synlett 1995, 573. (e) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
    • (1995) Synlett , pp. 573
    • Danheiser, R.L.1    Trova, M.P.2
  • 24
    • 0029552624 scopus 로고
    • For applications of this aromatic annulation strategy in the total synthesis of natural products, see: (a) Danheiser, R. L.; Casebier, D. S.; Loebach, J. L. Tetrahedron Lett. 1982, 33, 1149. (b) Danheiser, R. L.; Casebier, D. S.; Huboux, A. H. J. Org. Chem. 1994, 59, 4844. (c) Danheiser, R. L.; Helgason, A. L. J. Am. Chem. Soc. 1994, 116, 9471. (d) Danheiser, R. L.; Trova, M. P. Synlett 1995, 573. (e) Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
    • (1995) J. Org. Chem. , vol.60 , pp. 8341
    • Danheiser, R.L.1    Casebier, D.S.2    Firooznia, F.3
  • 29
    • 15644383603 scopus 로고    scopus 로고
    • See references cited in ref 13a
    • See references cited in ref 13a.
  • 31
    • 84990132418 scopus 로고
    • For reviews on the chemistry of cyclobutenones, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797. (b) Wong, H. N. C.; Lau, K.-L.; Tam, K.-F. Top. Curr. Chem. 1986, 733, 83. (c) Moore, H. W.; Yerxa, B. R. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: London, 1995; pp 81-162.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 797
    • Bellus, D.1    Ernst, B.2
  • 32
    • 0003749873 scopus 로고
    • For reviews on the chemistry of cyclobutenones, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797. (b) Wong, H. N. C.; Lau, K.-L.; Tam, K.-F. Top. Curr. Chem. 1986, 733, 83. (c) Moore, H. W.; Yerxa, B. R. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: London, 1995; pp 81-162.
    • (1986) Top. Curr. Chem. , vol.733 , pp. 83
    • Wong, H.N.C.1    Lau, K.-L.2    Tam, K.-F.3
  • 33
    • 0002225356 scopus 로고
    • Halton, B., Ed.; Jai Press: London
    • For reviews on the chemistry of cyclobutenones, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797. (b) Wong, H. N. C.; Lau, K.-L.; Tam, K.-F. Top. Curr. Chem. 1986, 733, 83. (c) Moore, H. W.; Yerxa, B. R. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; Jai Press: London, 1995; pp 81-162.
    • (1995) Advances in Strain in Organic Chemistry , pp. 81-162
    • Moore, H.W.1    Yerxa, B.R.2
  • 40
    • 84937248389 scopus 로고
    • The butenolide byproducts most likely result from reaction of the TAS-vinylketene with oxygen. For a related reaction, see: Zhao, D.-C.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 10980.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10980
    • Zhao, D.-C.1    Tidwell, T.T.2
  • 45
    • 0027404969 scopus 로고
    • (e) For a review on the application of silyl-substituted conjugated dienes in synthesis, see: Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349.
    • (1993) Synthesis , pp. 349
    • Luh, T.-Y.1    Wong, K.-T.2
  • 46
    • 15644363593 scopus 로고    scopus 로고
    • note
    • c.
  • 51
    • 33845559839 scopus 로고
    • For examples, see: (a) Brady, W. T.; Saidi, K. J. Org. Chem. 1979, 44, 733. (b) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synlett 1992, 31.
    • (1979) J. Org. Chem. , vol.44 , pp. 733
    • Brady, W.T.1    Saidi, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.