메뉴 건너뛰기




Volumn 38, Issue 17, 1999, Pages 2583-2585

An unprecedented domino double allylsilane [3 + 2] cycloaddition/Wagner- Meerwein rearrangement/Friedel-Crafts alkylation/elimination reaction sequence leading to a novel pentacyclic ring system

Author keywords

Allylsilanes; Cycloadditions; Diastereoselective synthesis; Domino reactions; Rearrangements

Indexed keywords

ACID; ALLYL COMPOUND; HETEROCYCLIC COMPOUND; SILANE DERIVATIVE;

EID: 0039573366     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990903)38:17<2583::AID-ANIE2583>3.0.CO;2-1     Document Type: Article
Times cited : (28)

References (31)
  • 3
    • 0027318323 scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3845
    • Danheiser, R.L.1    Takahashi, T.2    Bertók, B.3    Dixon, B.R.4
  • 4
    • 0001159938 scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1993) J. Org. Chem. , vol.58 , pp. 2345
    • Panek, J.S.1    Jain, N.F.2
  • 5
    • 0028137704 scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1994) Tetrahedron , vol.50 , pp. 1073
    • Wu, M.-J.1    Yeh, J.-Y.2
  • 6
    • 0000890707 scopus 로고    scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1996) J. Org. Chem. , vol.61 , pp. 3230
    • Brengel, G.P.1    Meyers, A.I.2
  • 7
    • 0041102806 scopus 로고    scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1997) Chem. Eur. J. , vol.3 , pp. 538
    • Knölker, H.-J.1    Foitzik, N.2    Goesmann, H.3    Graf, R.4    Jones, P.G.5    Wanzl, G.6
  • 8
    • 0000446955 scopus 로고    scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1997) Organometallics , vol.16 , pp. 5158
    • Choi, G.M.1    Yeon, S.H.2    Jin, J.3    Yoo, B.R.4    Jung, I.N.5
  • 9
    • 33748717992 scopus 로고    scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1998) J. Chem. Soc. Perkin Trans. I , pp. 2121
    • Akiyama, T.1    Hoshi, E.2    Fujiyoshi, S.3
  • 10
    • 0344820772 scopus 로고    scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1999) Synthesis , pp. 145
    • Knölker, H.-J.1    Foitzik, N.2    Gabler, C.3    Graf, R.4
  • 11
    • 0033617134 scopus 로고    scopus 로고
    • Further applications: a) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845; b) J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; c) M.-J. Wu, J.-Y. Yeh, Tetrahedron 1994, 50, 1073; d) G. P. Brengel, A. I. Meyers, J. Org. Chem. 1996, 61, 3230; e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538; f) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158; g) T. Akiyama, E. Hoshi, S. Fujiyoshi, J. Chem. Soc. Perkin Trans. I 1998, 2121; h) H.-J. Knölker, N. Foitzik, C. Gabler, R. Graf, Synthesis 1999, 145; i) H.-J. Knölker, N. Foitzik, O. Schmitt, Tetrahedron Lett. 1999, 40, 3557.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3557
    • Knölker, H.-J.1    Foitzik, N.2    Schmitt, O.3
  • 12
    • 0001782321 scopus 로고    scopus 로고
    • Reviews: I. Fleming, Chemtracts: Org. Chem. 1996, 9, 1; K. Tamao in Advances in Silicon Chemistry, Vol. 3, JAI Press, Greenwich (CT), 1996, p. 1; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
    • (1996) Chemtracts: Org. Chem. , vol.9 , pp. 1
    • Fleming, I.1
  • 13
    • 0002437012 scopus 로고    scopus 로고
    • JAI Press, Greenwich (CT)
    • Reviews: I. Fleming, Chemtracts: Org. Chem. 1996, 9, 1; K. Tamao in Advances in Silicon Chemistry, Vol. 3, JAI Press, Greenwich (CT), 1996, p. 1; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
    • (1996) Advances in Silicon Chemistry , vol.3 , pp. 1
    • Tamao, K.1
  • 14
    • 0030007621 scopus 로고    scopus 로고
    • Reviews: I. Fleming, Chemtracts: Org. Chem. 1996, 9, 1; K. Tamao in Advances in Silicon Chemistry, Vol. 3, JAI Press, Greenwich (CT), 1996, p. 1; G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
    • (1996) Tetrahedron , vol.52 , pp. 7599
    • Jones, G.R.1    Landais, Y.2
  • 15
    • 85064604194 scopus 로고
    • H.-J. Knölker, G. Wanzl, Synlett 1995, 378; H.-J. Knölker, P. G. Jones, G. Wanzl, Synlett 1998, 613.
    • (1995) Synlett , pp. 378
    • Knölker, H.-J.1    Wanzl, G.2
  • 17
    • 0004198491 scopus 로고
    • Wiley, Chichester
    • Reviews: T.-L. Ho, Tandem Organic Reactions, Wiley, Chichester, 1992; L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
    • (1992) Tandem Organic Reactions
    • Ho, T.-L.1
  • 18
    • 0001237986 scopus 로고
    • Reviews: T.-L. Ho, Tandem Organic Reactions, Wiley, Chichester, 1992; L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
    • (1993) Angew. Chem. , vol.105 , pp. 137
    • Tietze, L.F.1    Beifuss, U.2
  • 19
    • 33750173220 scopus 로고
    • Reviews: T.-L. Ho, Tandem Organic Reactions, Wiley, Chichester, 1992; L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
    • (1993) Angew. Chem. int Ed. Engl. , vol.32 , pp. 131
  • 20
    • 7044235263 scopus 로고    scopus 로고
    • Reviews: T.-L. Ho, Tandem Organic Reactions, Wiley, Chichester, 1992; L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
    • (1996) Chem. Rev. , vol.96 , pp. 115
    • Tietze, L.F.1
  • 23
    • 33748231662 scopus 로고
    • H.-J. Knölker, G. Baum, R. Graf, Angew. Chem. 1994, 106, 1705; Angew. Chem. Int. Ed. Engl. 1994, 33, 1612.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1612
  • 26
    • 0345676204 scopus 로고    scopus 로고
    • note
    • 26: C 90.59, H 9.41; found: C 90.23, H 9.21.
  • 27
  • 29
    • 0344813390 scopus 로고    scopus 로고
    • note
    • -3. All hydrogen atoms were determined by Fourier difference calculation and refined sotropically. Programs: G. M. Sheldrick, SHELXS-86 (Göttingen, 1986), SHELXL-93 (Göttingen, 1993); E. Keller, SCHAKAL-97 (Freiburg im Breisgau, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-116375 (6) and -132639 (9). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 31
    • 0004545165 scopus 로고
    • I. Fleming, D. Marchi, S. K. Patel, J. Chem. Soc. Perkin Trans. I 1981, 2518; H.-F. Chow, I. Fleming, Tetrahedron Lett. 1985, 26, 397.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 397
    • Chow, H.-F.1    Fleming, I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.