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Volumn 37, Issue 12, 1998, Pages 1734-1736

Ring-closing metathesis of functionalized acetylene derivatives: A new entry into cycloalkynes

Author keywords

Alkylidyne complexes; Alkynes; Macrocycles; Metathesis; Tungsten

Indexed keywords


EID: 0038731101     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1734::AID-ANIE1734>3.0.CO;2-6     Document Type: Article
Times cited : (194)

References (64)
  • 3
    • 0030771019 scopus 로고    scopus 로고
    • a) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2036
  • 12
    • 0031471863 scopus 로고    scopus 로고
    • f) A. Fürstner, D. Koch, K. Langemann, W. Leitner, C. Six, Angew. Chem. 1997, 109, 2562; Angew. Chem. Int. Ed. Engl. 1997, 36, 2466;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2466
  • 22
    • 0030738752 scopus 로고    scopus 로고
    • g) B. Mohr, M. Weck, J-P. Sauvage, R. H. Grubbs, Angew. Chem. 1997, 109, 1365; Angew. Chem. Int. Ed. Engl. 1997, 36, 1308;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1308
  • 25
    • 0030850057 scopus 로고    scopus 로고
    • For leading references on the synthesis of epothilone and analogues by RCM see a) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolaou, Angew. Chem. 1997, 109, 170; Angew. Chem. Int. Ed. Engl. 1997, 36, 166;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 166
  • 27
    • 0030445213 scopus 로고    scopus 로고
    • b) K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, Z. Yang, Angew. Chem. 1996, 108, 2554; Angew. Chem. Int. Ed. Engl. 1996, 35, 2399;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2399
  • 29
    • 0030894922 scopus 로고    scopus 로고
    • c) D. Schinzer, A. Limberg, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543; Angew. Chem. Int. Ed. Engl. 1997, 36, 523;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 523
  • 33
    • 0001768322 scopus 로고    scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12388
    • Kinoshita, A.1    Sakakibara, N.2    Mori, M.3
  • 34
    • 0030795542 scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1991) Tetrahedron , vol.53 , pp. 10603
    • Hammer, K.1    Undheim, K.2
  • 35
    • 0030796080 scopus 로고    scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1997) Chem. Commun. , pp. 1375
    • Barrett, A.G.M.1    Baugh, S.P.D.2    Braddock, D.C.3    Flack, K.4    Gibson, V.C.5    Procopiou, P.A.6
  • 36
    • 0000426668 scopus 로고    scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1997) Angew. Chem. , vol.109 , pp. 2628
    • Stragies, R.1    Schuster, M.2    Blechert, S.3
  • 37
    • 0031467515 scopus 로고    scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2518
  • 38
    • 0029956640 scopus 로고    scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1996) J. Org. Chem. , vol.61 , pp. 8356
    • Kinoshita, A.1    Mori, M.2
  • 39
    • 0001354464 scopus 로고    scopus 로고
    • Ene-yne metathesis reactions constitute notable exceptions; see [3 f] and a) A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12 388; b) K. Hammer, K. Undheim, Tetrahedron 1991, 53, 10603; c) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, P. A. Procopiou, Chem. Commun. 1997, 1375; d) R. Stragies, M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2628; Angew. Chem. Int. Ed. Engl. 1997, 36, 2518; e) A. Kinoshita, M. Mori, J. Org. Chem. 1996, 61, 8356; f) S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073.
    • (1996) J. Org. Chem. , vol.61 , pp. 1073
    • Kim, S.-H.1    Zuercher, W.J.2    Bowden, N.B.3    Grubbs, R.H.4
  • 41
    • 0000018360 scopus 로고
    • a) For the first examples of alkyne metathesis reactions with a defined alkylidyne catalyst see J. H. Wengrovius, J. Sancho, R. R. Schrock, J. Am. Chem. Soc. 1981, 103, 3932; b) Reviews: R. R. Schrock, Polyhedron 1995, 14, 3177; c) R. R. Schrock, Acc. Chem. Res. 1986, 19, 342; d) K. Weiss in Carbyne Complexes (Eds.: H. Fischer, P. Hofmann, F. R. Kreissl, R. R. Schrock, U. Schubert, K. Weiss), VCH, Weinheim. 1988 p 205.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3932
    • Wengrovius, J.H.1    Sancho, J.2    Schrock, R.R.3
  • 42
    • 11544274511 scopus 로고
    • a) For the first examples of alkyne metathesis reactions with a defined alkylidyne catalyst see J. H. Wengrovius, J. Sancho, R. R. Schrock, J. Am. Chem. Soc. 1981, 103, 3932; b) Reviews: R. R. Schrock, Polyhedron 1995, 14, 3177; c) R. R. Schrock, Acc. Chem. Res. 1986, 19, 342; d) K. Weiss in Carbyne Complexes (Eds.: H. Fischer, P. Hofmann, F. R. Kreissl, R. R. Schrock, U. Schubert, K. Weiss), VCH, Weinheim. 1988 p 205.
    • (1995) Polyhedron , vol.14 , pp. 3177
    • Schrock, R.R.1
  • 43
    • 0000677664 scopus 로고
    • a) For the first examples of alkyne metathesis reactions with a defined alkylidyne catalyst see J. H. Wengrovius, J. Sancho, R. R. Schrock, J. Am. Chem. Soc. 1981, 103, 3932; b) Reviews: R. R. Schrock, Polyhedron 1995, 14, 3177; c) R. R. Schrock, Acc. Chem. Res. 1986, 19, 342; d) K. Weiss in Carbyne Complexes (Eds.: H. Fischer, P. Hofmann, F. R. Kreissl, R. R. Schrock, U. Schubert, K. Weiss), VCH, Weinheim. 1988 p 205.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 342
    • Schrock, R.R.1
  • 44
    • 0344016148 scopus 로고
    • (Eds.: H. Fischer, P. Hofmann, F. R. Kreissl, R. R. Schrock, U. Schubert, K. Weiss), VCH, Weinheim
    • a) For the first examples of alkyne metathesis reactions with a defined alkylidyne catalyst see J. H. Wengrovius, J. Sancho, R. R. Schrock, J. Am. Chem. Soc. 1981, 103, 3932; b) Reviews: R. R. Schrock, Polyhedron 1995, 14, 3177; c) R. R. Schrock, Acc. Chem. Res. 1986, 19, 342; d) K. Weiss in Carbyne Complexes (Eds.: H. Fischer, P. Hofmann, F. R. Kreissl, R. R. Schrock, U. Schubert, K. Weiss), VCH, Weinheim. 1988 p 205.
    • (1988) Carbyne Complexes , pp. 205
    • Weiss, K.1
  • 47
    • 0030980103 scopus 로고    scopus 로고
    • b) K. Weiss, A. Michel, E-M. Auth, U. H. F. Bunz, T. Mangel, K. Müllen, Angew. Chem. 1997, 109, 522; Angew. Chem. Int. Ed. Engl. 1997, 36, 506;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 506
  • 53
    • 0003391883 scopus 로고
    • VCH, Weinheim
    • 4]. Because of the symmetry of this molecule, the stereochemical assignment is based on the characteristic shift of its allylic C-atoms (δ = 27.3). In the case of Z-alkenes these positions resonate in the range δ = 27-28; but for E-alkenes in the range δ = 32-33; cf.: E. Breitmaier, W. Voelter, Carbon-13 NMR Spectroscopy, 3rd ed., VCH, Weinheim, 1987, 192.
    • (1987) Carbon-13 NMR Spectroscopy, 3rd Ed. , pp. 192
    • Breitmaier, E.1    Voelter, W.2
  • 54
    • 0030983374 scopus 로고    scopus 로고
    • b) The hydroboration/protonation sequence is superior to Lindlar hydrogenation in terms of selectivity: A. Fürstner, G. Seidel, J. Org. Chem. 1997, 62, 2332.
    • (1997) J. Org. Chem. , vol.62 , pp. 2332
    • Fürstner, A.1    Seidel, G.2
  • 59
    • 84920310655 scopus 로고    scopus 로고
    • note
    • GC and NMR investigations suggest that a single isomer is formed; however, we cannot yet determine whether it is the head - head or the head-tail connected cyclodimeric product.
  • 61
    • 0029088989 scopus 로고
    • b) For a new synthesis of cycloalkynes and a compilation of the recent literature see J. Boivin, S. Huppé, S. Z. Zard, Tetrahedron Lett. 1995, 36, 5737.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5737
    • Boivin, J.1    Huppé, S.2    Zard, S.Z.3


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